Abstract
This chapter begins with the nucleophilic reactions of fullerenes, in which Grignard reagents, alkyllithium, and other carbon nucleophiles, as well as silicon and phosphorous nucleophiles, have been employed for the synthesis of a variety of fullerene adducts. In some cases, multiple adducts have been synthesized regioselectively. The second part deals with electrophilic reactions, although reported examples of these reactions are still limited. The third part is devoted to addition–elimination reactions, which have been recognized as one of the most powerful methodologies to construct methanofullerenes. Other types of cycloadducts can also be obtained by modifying the substrates. Carbenes and silylenes are also reactive toward fullerenes; this reactivity is described in the fourth part. A variety of 1,3-dipolar cycloadditions, including the well-known Prato reactions, are summarized in the fifth part. The sixth part deals with nitrene additions, as these are relevant to 1,3-dipolar cycloadditions. The seventh part is devoted to phosphine-mediated reactions. Notably, azafulleroids and azamethanofullerenes have also been prepared via 1,3-dipolar cycloadditions followed by N2 extrusion. Several examples of [2 + 2] cycloadditions are described in the eighth part. Finally, a variety of Diels–Alder reactions are summarized in the final part. Noteworthily, some Diels–Alder cycloadducts obtained from the reactions of fullerenes with nitrogen-containing aromatic compounds provide useful precursors for the preparation of open-cage fullerenes and endohedral fullerenes. In addition, the reversibility of the Diels–Alder reaction of C60 with 9,10-dimethylanthracene has been applied to achieve the regioselective synthesis of hexaadducts.
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References
Hirsch A, Grösser T, Skiebe A, Soi A (1993) Synthesis of isomerically pure organodihydrofullerenes. Chem Ber 126(4):1061–1067
Fagan PJ, Krusic PJ, Evans DH, Lerke SA, Johnston E (1992) Synthesis, chemistry, and properties of a monoalkylated buckminsterfullerene derivative, t-BuC60 anion. J Am Chem Soc 114(24):9697–9699
Morton JR, Preston KF, Krusic PJ, Hil A, Wasserman E (1992) The dimerization of RC60 radicals. J Am Chem Soc 114(13):5454–5455
Hirsch A, Soi A, Karfunkel HR (1992) Titration of C60: a method for the synthesis of organofullerenes. Angew Chem, Int Ed Engl 31(6):766–768
Fukuzumi S, Suenobu T, Hirasaka T, Arakawa R, Kadish KM (1998) Formation of C60 adducts with two different alkyl groups via combination of electron transfer and SN2 reactions. J Am Chem Soc 120(36):9220–9227
Nagashima H, Terasaki H, Kimura E, Nakajima K, Itoh K (1994)
Nagashima H, Terasaki H, Saito Y, Jinno K, Itoh K (1995) Chlorosilanes and silyl triflates containing C60 as a partial structure. A versatile synthetic entry linking the C60 moieties with alcohols, phenols, and silica. J Org Chem 60(16):4966–4967
Matsuo Y, Nakamura E (2006) Synthesis of trialkyl[60]fullerene C60(CH2SiMe3)3H and its potassium and rhodium(I) complexes. Inorg. Chim. Acta 359(6):1979–1982
Matsuo Y, Iwashita A, Abe Y, Li C-Z, Matsuo K, Hashiguchi M, Nakamura E (2008) Regioselective synthesis of 1,4-di(organo)[60]fullerenes through DMF-assisted monoaddition of silylmethyl Grignard reagents and subsequent alkylation reaction. J Am Chem Soc 130(46):15429–15436
Komatsu K, Murata Y, Takimoto N, Mori S, Sugita N, Wan TSM (1994) Synthesis and properties of the first acetylene derivatives of C60. J Org Chem 59(20):6101–6102
Anderson HL, Faust R, Rubin Y, Diederich F (1994) Fullerene–acetylene hybrids: on the way to synthetic molecular carbon allotropes. Angew Chem, Int Ed Engl 33(13):1366–1368
Timmerman P, Anderson HL, Faust R, Nierengarten J-F, Habicher T, Seiler P, Diederich F (1996) Fullerene-acetylene hybrids: towards a novel class of molecular carbon allotropes. Tetrahedron 52(14):4925–4947
Murata Y, Motoyama K, Komatsu K, Wan TSM (1996) Synthesis, properties, and reactions of a stable carbanion derived from alkynyldihydrofullerene: 1-Octynyl-C60 carbanion. Tetrahedron 52(14):5077–5090
Keshavarz-K M, Knight B, Srdanov G, Wudl F (1995) Cyanodihydrofullerenes and dicyanodihydrofullerene: the first polar solid based on C60. J Am Chem Soc 117(45):11371–11372
Murata Y, Komatsu K, Wan TSM (1996) The reaction of [60]fullerene with lithium fluorenide: Formation of a novel 1,4-adduct of [60]fullerene. Tetrahedron Lett 37(39):7061–7064
Murata Y, Shiro M, Komatsu K (1997) Synthesis, X-ray structure, and properties of the first tetrakisadduct of fullerene C60 having a fulvene-type π-system on the spherical surface. J Am Chem Soc 119(34):8117–8118
Sawamura M, Iikura H, Nakamura E (1996) The first pentahaptofullerene metal complexes. J Am Chem Soc 118(50):12850–12851
Matsuo Y, Tahara K, Morita K, Matsuo K, Nakamura E (2007) Regioselective eightfold and tenfold additions of a pyridine-modified organocopper reagent to [60]fullerene. Angew Chem Int Ed 46(16):2844–2847
Li D, Li Z-J, He F-G, Geng C, Gao X (2019) Synthesizing 1,23-C60 adducts with improved efficiency: a type of stable and highly soluble C60 derivatives. J Org Chem 84(22):14679–14687
Kusukawa T, Ando W (1996) Reactions of silyllithium with C60: isolation and X-ray crystallographic characterization of an unusual bissilylated-C60 adduct. Angew Chem, Int Ed Engl 35(12):1315–1317
Kusukawa T, Ando W (1998) Substituents effects on the addition of silyllithium and germyllithium to C60. J Organomet Chem 561:109–120
Yamago S, Yanagawa M, Nakamura E (1994) Tertiary phosphines and P-chiral phosphinites bearing a fullerene substituent. J Chem Soc, Chem Commun 18:2093–2094
Kitagawa T, Sakamoto H, Takeuchi K (1999) Electrophilic addition of polychloroalkanes to C60: direct observation of aklylfullerenyl cation intermediates. J Am Chem Soc 121(17):4298–4299
Kitagawa T, Lee Y, Hanamura M, Sakamoto H, Konno H, Takeuchi K, Komatsu K (2002) Nucleophilic substitution of alkylchlorodihydro[60]fullerenes: thermodynamic stabilities of alkylated C60 cation intermediates. Chem Comm 24:3062–3063
Matsuo Y, Yu Y, Yang X-Y, Ueno H, Okada H, Shibuya H, Choi YS, Jin YW (2019) Synthesis of benzothieno[60]fullerenes through fullerenyl cation intermediates. J Org Chem 84(10):6270–6277
Lin H-S, Matsuo Y (2018) Functionalization of [60]fullerene through fullerene cation intermediates. Chem Commun 54(80):11244–11259
Biglova YN, Mustafin AG (2019) Nucleophilic cyclopropanation of [60]fullerene by the addition–elimination mechanism. RSC Adv 9(39):22428–22498
Bingel C (1993) Cyclopropanierung von fullerenen. Chem Ber 126(8):1957–1959
Hirsch A, Lamparth, Karfunkel HR (1994) Fullerene chemistry in three dimensions: Isolation of seven regioisomeric bisadducts and chiral trisadducts of C60 and di(ethoxycarbonyl)methylene. Angew Chem, Int Ed Engl 33(4):437–438
Camps X, Hirsch A (1997) Efficient cyclopropanation of C60 starting from malonates. J Chem Soc, Perkin Trans 1(11):1595–1596
Nierengarten J-F, Herrmann A, Tykwinski RR, Rüttimann M, Diederich F (1997) Methanofullerene molecular scaffolding: towards C60-substituted poly(triacetylenes) and expanded radialenes, preparation of C60–C70 hybrid derivative, and a novel macrocyclization reaction. Helv Chim Acta 80(1):293–316
Feng L, Nakahodo T, Wakahara T, Tsuchiya T, Maeda Y, Akasaka T, Kato T, Horn E, Yoza K, Mizorogi N, Nagase S (2005) A singly bonded derivative of endohedral metallofullerene: La@C82CBr(COOC2H5)2. J Am Chem Soc 127(49):17136–17137
Anderson HL, Faust R, Rubin Y, Diederich F (1994) Fullerene–acetylene hybrids: On the way to synthetic molecular carbon allotropes. Angew Chem, Int Ed Engl 33(13):1366–1368
Wang Y, Cao J, Schuster DI, Wilson SR (1995) A superior synthesis of [6,6]-methanofullerenes: The reaction of sulfonium ylides with C60. Tetrahedron Lett 36(38):6843–6846
Wang G-W, Li J-X, Xu Y (2008) Synthesis of C60-fused tetrahydrothiophene derivatives via nucleophilic cycloaddition of thiocyanates. Org Biomol Chem 6(16):2995–2999
Ball GE, Burley GA, Chaker L, Hawkins BC, Williams JR, Keller PA, Pyne SG (2005) Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions. J Org Chem 70(21):8572–8574
Tsuda M, Ishida T, Nogami T, Kurono S, Ohashi M (1993) C61Cl2. Synthesis and characterization of dichlorocarbene adducts of C60. Tetrahedron Lett 34(43):6911–6912
Benito AM, Darwish AD, Kroto HW, Meidine MF, Taylor R, Walton DRM (1996) Synthesis and characterization of the methanofullerenes, C60(CHCN) and C60(CBr2). Tetrahedron Lett 37(7):1085–1086
Osterodt J, Vögtle V (1996) C61Br2: a new synthesis of dibromomethanofullerene and mass spectrometric evidence of the carbon allotropes C121 and C122. Chem Comm 4:547–548
Yinghuai Z, Bahnmueller S, Chibun C, Carpenter K, Hosmane NS, Maguire JA (2003) An effective system to synthesize methanofullerenes: substrate–ionic liquid–ultrasonic irradiation. Tetrahedron Lett 44(29):5473–5476
Gao X, Ishimura K, Nagase S, Chen Z (2009) Dichlorocarbene addition to C60 from the trichloromethyl anion: carbene mechanism of Bingel mechanism? J Phys Chem A 113(15):3673–3676
Tokuyama H, Nakamura M, Nakamura E (1993) [1 + 2] and [3 + 2] Cycloaddition reactions of vinylcarbenes with C60. Tetrahedron Lett 34(46):7429–7432
Tokuyama H, Isobe H, Nakamura E (1995) Methano- and propanofullerenes by [1 + 2] and [3 + 2] cycloadditions of vinylcarbene species. Bull Chem Soc Jpn 68(3):935–941
Isobe H, Tokuyama H, Sawamura M, Nakamura E (1997) Synthetic and computational studies on symmetry-defined double cycloaddition of a new tris-annulating reagent to C60. J Org Chem 62(15):5034–5041
Suzuki T, Maruyama Y, Akasaka T, Ando W, Kobayashi K, Nagase S (1994) Redox properties of organofullerenes. J Am Chem Soc 116(4):1359–1363
Romanova IP, Bogdanov AV, Mironov VF, Shaikhutdinova GR, Larionova OA, Latypov SK, Balandina AA, Yakhvarov DG, Gubaidullin AT, Saifina AF, Sinyashin OG (2011) Deoxygenation of some α-dicarbonyl compounds by tris(diethylamino)phosphine in the presence of fullerene C60. J Org Chem 76(8):2548–2557
Nikawa H, Nakahodo T, Tsuchiya T, Wakahara T, Rahman GMA, Akasaka T, Maeda Y, Liu MTH, Meguro A, Kyushin S, Matsumoto H, Mizorogi N, Nagase S (2005) S-Heterocyclic carbene with a disilane backbone. Angew Chem Int Ed 44(46):7567–7570
Kako M, Arikawa Y, Kanzawa S, Yamada M, Maeda Y, Furukawa M, Akasaka T (2019) Addition of S-heterocyclic carbenes to fullerenes: Formation and characterization of dithiomethano-bridged derivatives. Helv Chim Acta 102:e1900064
Li H, Risko C, Seo JH, Campbell C, Wu G, Brédas J-L, Bazan GC (2011) Fullerene–carbene Lewis acid–base adducts. J Am Chem Soc 133(32):12410–12413
Chen M, Bao L, Ai M, Shen W, Lu X (2016) Sc3N@Ih-C80 as a novel Lewis acid to trap abnormal N-heterocyclic carbenes: the unprecedented formation of a singly bonded [6,6,6]-adduct. Chem Sci 7(3):2331–2334
Komatsu K, Kagayama A, Murata Y, Sugita N, Kobayashi K, Nagase S, Wan TSM (1993) Reaction of C60 with chlorophenyldiazirine. Chem Lett 22(12):2163–2166
Yamada M, Akasaka T, Nagase S (2013) Carbene additions to fullerenes. Chem Rev 113(9):7209–7264
Akasaka T, Ando W, Kobayashi K, Nagase S (1993) Reaction of C60 with silylene, the first fullerene silirane derivative. J Am Chem Soc 115(4):1605–1606
Akasaka T, Mitsuhida E, Ando W, Kobayashi K, Nagase S (1995) Regioselective addition of silylene on to [70]fullerene. J Chem Soc, Chem Commun 15:1529–1530
Maggini M, Scorrano G, Prato M (1993) Addition of azomethine ylides to C60: synthesis, characterization, and functionalization of fullerene pyrrolidienes. J Am Chem Soc 115(21):9798–9799
Prato M, Maggini M (1998) Fulleropyrrolidines: a family of full-fledged fullerene derivatives. Acc Chem Res 31(9):519–526
Izquierdo M, Osuna S, Filippone S, Martín-Domenech Á, Solá M, Martín N (2009) H-Bond-assisted regioselective (cis-1) intramolecular nucleophilic addition of the hydroxyl group to [60]fullerene. J Org Chem 74(4):1480–1487
Izquierdo M, Osuna S, Filippone S, Martín-Domenech Á, Solá M, Martín N (2009) Regioselective intramolecular nucleophilic addition of alcohols to C60: one-step formation of a cis-1 bicyclic-fused fullerene. J Org Chem 74(16):6253–6259
Izquierdo M, Osuna S, Filippone S, Martín-Domenech Á, Solá M, Martín N (2009) On the regioselective intramolecular nucleophilic addition of thiols to C60. Eur J Org Chem 35:6231–6238
Martín N, Altable M, Filippone F, Marín-Domenech Á, Güell M, Solá M (2006) Thermal [2 + 2] Intramolecular cycloadditions of fuller-1,6-enynes. Angew Chem Int Ed 45(9):1439–1442
Altable M, Filippone S, Martín-Domenech Á, Güell M, Solá M, Martín N (2006) Intramolecular ene reaction of 1,6-fullerenynes: a new synthesis of allenes. Org Lett 8(26):5959–5962
Martín N, Altable M, Filippone S, Martín-Domenech Á (2004) Highly efficient Pauson–Khand reaction with C60: regioselective synthesis of unprecedented cis-1 biscycloadducts. Chem Commun 11:1338–1339
Martin N, Altable M, Filippone S, Martin-Domeneck A, Poater A, Sola M (2005) Regioselective intramolecular Pauson–Khand reactions of C60: an electrochemical study and theoretical underpinning. Chem Eur J 11(9):2716–2729
Ito S, Tokimaru Y, Nozaki K (2015) Isoquinolino[4,3,2-de]phenanthridine: synthesis and its use in 1,3-dipolar cycloadditions to form nitrogen-containing polyaromatic hydrocarbons. Chem Commun 51(1):221–224
Jagerovic N, Elguero J, Aubagnac J-L (1996) Cycloaddition of tetracyanoethene oxide with [60]fullerene. J Chem Soc, Perkin Trans 1(6):499
Meier MS, Poplawska M (1993) Addition of nitrile oxides to C60: formation of isooxazoline derivatives of fullerenes. J Org Chem 58(17):4524–4525
Meier MS, Poplawska M (1996) The addition of nitrile oxides to C60. Tetrahedron 52(14):5043–5042
Da Ros T, Prato M, Novello F, Maggini M, De Amici M, De Micheli C (1997) Cycloaddition of nitrile oxides to [60]fullerene. Chem Commun 1:59–60
Illescas BM, Martín N (2000) [60]Fullerene adducts with improved electron acceptor properties. J Org Chem 65(19):5986–5995
Matsubara Y, Tada H, Nagase S, Yoshida Z (1995) Intramolecular charge transfer interaction in 1,3-diphenyl-2-pyrazoline ring-fused C60. J Org Chem 60(17):5372–5373
Delgado JL, de la Cruz P, Lopez-Arza V, Langa F, Gan Z, Araki Y, Ito O (2005) Synthesis and photoinduced intermolecular electronic acceptor ability of pyrazolo[60]fullerenes vs tetrathiafulvalene. Bull Chem Soc Jpn 78(8):1500–1507
Ishida H, Itoh K, Ohno M (2001) 1,3-Dipolar cycloaddition reaction of [60]fullerene with thiocarbonyl ylide and synthetic application of the cycloadduct. Tetrahedron 57(9):1737–1747
Prato M, Suzuki T, Foroudian H, Li Q, Khemani K, Wudl F, Leonetti J, Little RD, White T, Rickborn B, Yamago S, Nakamura E (1993) [3 + 2] and [4 + 2] Cycloadditions of C60. J Am Chem Soc 115(4):1594–1595
Suzuki T, Li Q, Khemani KC, Wudl F, Almarsson Ö (1991) Systematic inflation of buckminsterfullerene C60: synthesis of diphenyl fulleroids C61 to C66. Science 254(5035):1186–1188
Suzuki T, Li Q, Khemani KC, Wudl F, Almarsson Ö (1992) Synthesis of m-phenylene- and p-phenylenebis(phenylfulleroids): two-pearl sections of pearl necklace polymers. J Am Chem Soc 114(18):7300–7301
Wudl F (1992) The chemical properties of buckminsterfullerene (C60) and the birth and infancy of fulleroids. Acc Chem Res 25(3):157–161
Suzuki T, Li Q, Khemani KC, Wudl F (1992) Dihydrofulleroid H2C61: synthesis and properties of the parent fulleroid. J Am Chem Soc 114(18):7301–7302
Smith AB III, Strongin RM, Brard L, Furst GT, Romanow WJ, Owens KG, King RC (1993) 1,2-Methanobuckminsterfullerene (C61H2), the parent fullerene cyclopropane: synthesis and structure. J Am Chem Soc 115(13):5829–5830
Hummelen JC, Knight BW, LePeq F, Wudl F (1995) Preparation and characterization of fulleroid and methanofullerene derivatives. J Org Chem 60(3):532–538
Heymann D, Bachilo SM, Weisman RB, Cataldo F, Fokkens RH, Nibbering NMM, Vis RD, Chibante LPF (2000) C60O3, A fullerene ozonide: synthesis and dissociation to C60O and O2. J Am Chem Soc 122(46):11473–11479
Weisman RB, Heymann D, Bachilo SM (2001) Synthesis and characterization of the “missing” oxide of C60: [5,6]-Open C60O. J Am Chem Soc 123(39):9720–9721
Prato M, Li QC, Wudl F, Lucchini V (1993) Addition of azides to C60: synthesis of azafulleroids. J Am Chem Soc 115(3):1148–1150
Grösser T, Prato M, Lucchini V, Hirsch A, Wudl F (1995) Ring expansion of the fullerene core by highly regioselective formation of diazafulleroids. Angew Chem, Int Ed Engl 34(12):1343–1345
Ulmer L, Mattay J (2003) Preparation and characterization of sulfonyl-azafulleroid and sulfonylaziridino-fullerene derivatives. Eur J Org Chem 15:2933–2940
Nakahodo T, Okada M, Morita H, Yoshimura T, Ishitsuka MO, Tsuchiya T, Maeda Y, Fujiwara H, Akasaka T, Gao X, Nagase S (2008) [2+1] Cycloaddition of nitrene onto C60 revisited: Interconversion between an aziridinofullerene and an azafulleroid. Angew Chem Int Ed 47(7):1298–1300
Okada M, Nakahodo T, Ishitsuka MO, Nikawa H, Tsuchiya T, Akasaka T, Fujie T, Yoshimura T, Slanina Z, Nagase S (2011) Highly regioselective synthesis of bis-aziridino[60]fullerene with sulfilimine. Chem Asian J 6(2):416–423
Yamaguchi H, Murata S, Akasaka T, Suzuki T (1997) Preparation and structure of a novel methano[60]fullerene containing a stable P-ylid. Tetrahedron Lett 38(20):3529–3530
Chen S-Y, Cheng R-L, Tseng C-K, Venkatachalam RK, Chen Y-C, Cheng C-H, Chuang S-C (2009) Fullerene derivatives incorporating phosphoramidous ylide and phosphoramidate: synthesis and Property. J Org Chem 74(13):4866–4869
Liou K-F, Cheng C-H (1995) Phosphine-mediated [2 + 2] cycloaddition of internal alk-2-ynoate and alk-2-ynone to [60]fullerene. J Chem Soc, Chem Commun 24:2473–2474
Hsiao T-Y, Chidambareswaran SK, Cheng C-H (1998) Novel bismethanofullerenes and ethenofullerene from the reaction of propiolates with C60 in the presence of triphenylphosphine. J Org Chem 63(23):8617–8620
Shu L-H, Sun W-Q, Zhang D-W, Wu S-H, Wu H-M, Xu J-F, Lao X-F (1997) Phosphine-catalyzed [3 + 2] cycloadditions of buta-2,3-dienoates with [60]fullerene. J Chem Soc, Chem Commun 1:79–80
Tseng P-Y, Chuang S-C (2013) Chemo-, regio- and stereoselective tricyclohexylphosphine-catalyzed [3 + 2] cycloaddition of enynes with [60]fullerene initiated by 1,4-Michael addition: Synthesis of cyclopenteno[60]fullerenes and their electrochemical properties. Adv Synth Cat 355(11-12):2165–2171
Wu A-J, Tseng P-Y, Hsu W-H, Chuang S-C (2016) Tricyclohexylphosphine-catalyzed cycloaddition of enynoates with [60]fullerene and the application of cyclopentenofullerenes as n-type materials in organic photovoltaics. Org Lett 18(2):224–227
Bildstein B, Schweiger M, Angleitner H, Kopacka H, Wurst K, Ongania K-H, Fontani M, Zanello P (1999) Tetraferrocenyl[5]cumulene, (Fc)2C=C=C=C=C=C(Fc)2: Synthesis, electrochemistry, and reactivity, including nickel(0)-promoted [3]ferrocenophane formation and [2+2] cycloaddition with fullerene C60. Organometallics 18(21):4286–4295
Yamago S, Takeichi A, Nakamura E (1994) Synthesis and [2 + 2] cycloaddition of dimethyleneketene acetals. Reaction with C60 and facile hydrolysis of the C–C bond connected to C60. J Am Chem Soc 116(3):1123–1124
Hoke SH II, Molstad J, Dilettato D, Jay DJ, Carlson D, Kahr B, Cooks RG (1992) Reaction of fullerenes and benzyne. J Org Chem 57(19):5069–5071
Ishida T, Shinozuka K, Nogami T, Sasaki S, Iyoda M (1995) First X-ray structural determination of fullerene [2+2] cycloadduct. Chem Lett 24(4):317–318
Nakamura Y, Takano N, Nishimura T, Yashima E, Sato M, Kudo T, Nishimura J (2001) First isolation and characterization of eight regioisomers for [60]fullerene–benzyne bisadducts. Org Lett 3(8):1193–1196
Meier MS, Wang G-W, Haddon RC, Brock CP, Lloyd MA, Selegue JP (1998) Benzyne adds across a closed 5–6 ring fusion in C70: evidence for bond delocalization in fullerenes. J Am Chem Soc 120(10):2337–2342
Lu X, Nikawa H, Tsuchiya T, Akasaka T, Toki M, Sawa H, Mizorogi N, Nagase S (2010) Nitrated benzyne derivatives of La@C82: addition of NO2 and its positional directing effect on the subsequent addition of benzynes. Angew Chem, Int Ed 49(3):594–597
Li FF, Pinzón JR, Mercado BQ, Olmstead MM, Balch AL, Echegoyen L (2011) [2 + 2] Cycloaddition reaction to Sc3N@Ih-C80. The formation of very stable [5,6]- and [6,6]-adducts. J Am Chem Soc 133(5):1563–1571
Ueda M, Sakaguchi T, Hayama M, Nakagawa T, Matsuo Y, Munechika A, Yoshida S, Yasuda H, Ryu I (2016) Regio- and stereo-selective intermolecular [2 + 2] cycloaddition of allenol esters with C60 leading to alkylidenecyclobutane-annulated fullerenes. Chem Comm 52(89):13175–13178
Yamada M, Ochi R, Yamamoto Y, Okada S, Maeda Y (2017) Tansition-metal-catalyzed divergent functionalization of [60]fullerene with propargylic esters. Org Biomol Chem 15(40):8499–8503
Tsuda M, Ishida T, Nogami T, Kurono S, Ohashi M (1993) Isolation and characterization of Diels–Alder adducts of C60 with anthracene and cyclopentadiene. J Chem Soc, Chem Commun 16:1296–1298
Pang LSK, Wilson MA (1993) Reactions of C60 and C70 with cyxlopentadiene. J Phys Chem 97(26):6761–6763
Kräutler B, Maynollo J (1996) Diels–Alder reactions of the [60]fullerene functionalizing a carbon sphere with flexibly and with rigidly bound addends. Tetrahedron 52(14):5033–5042
Illescas B, Martín N, Seoane C, de la Cruz P, Langa F, Wudl F (1995) A facile formation of electroactive fullerene adducts from sultines via a Diels–Alder reaction. Tetrahedron Lett 36(45):8307–8310
Zhang X, Foote CS (1994) Reaction of C60 with benzocyclobutenol: expeditious route to fullerene adducts. J Org Chem 59(18):5235–5238
Belik P, Gügel A, Spickerman J, Müllen K (1993) Reaction of buckminsterfullerene with ortho-quinodimethane: a new access to stable C60 derivatives. Angew Chem, Int Ed Engl 32(1):78–80
Rubin Y, Khan S, Freedberg DI, Yeretzian C (1993) Synthesis and X-ray structure of a Diels–Alder adduct of C60. J Am Chem Soc 115(1):344–345
Markoulides MS, Ioannou GI, Manos MJ, Chronakis N (2013) One-pot thermally chemocontrolled double Diels–Alder strategies. A route to [4 + 2] functionalization/[4 + 2] derivatization of C60. RSC Adv 3(14):4750–4756
Ohno M, Azuma T, Kojima S, Shirakawa Y, Eguchi S (1996) An efficient functionalization of [60]fullerene. Diels–Alder reaction using 1,3-butadienes substituted with electron-withdrawing and electron-donating (silyloxy) groups. Tetrahedron 52(14):4983–4994
Mikami K, Matsumoto S, Okubo Y, Fujitsuka M, Ito O, Suenobu T, Fukuzumi S (2000) Stepwise bond formation in photochemical and thermal Diels–Alder reactions of C60 with Danishefsky’s dienes. J Am Chem Soc 122(10):2236–2243
Arce MJ, Viado AL, An Y-Z, Khan SI, Rubin Y (1996) Triple scission of a six-membered ring on the surface of C60 via consecutive pericyclic reactions and oxidative cobalt insertion. J Am Chem Soc 118(15):3775–3776
Martín N, Martinez-Grau A, Sanchez L, Seoane C, Torres M (1998) The first hetero-Diels–Alder reaction of C60 with 1-azadienes. Synthesis of tetrahydro[2’,3’:1,2][60]fullerene derivatives. J Org Chem 63(22):8074–8076
Ohno M, Azuma T, Eguchi S (1993) Buckminsterfullerene C60 – o-quinone methide cycloadduct. Chem Lett 22(11):1833–1834
Ohno M, Kojima S, Shirakawa Y, Eguchi S (1995) Hetero-diels-alder reaction of fullerene: Synthesis of thiochroman-fused C60 with o-thioquinone methide and oxidation to its S-oxides. Tetrahedron Lett 36(38):6899–6902
Miller GP, Tetreau MC (2000) Facile, completely regioselective 1,4-hydrogenations of C60-diaryltetrazine monoadducts. Org Lett 2(20):3091–3094
Miller GP, Tetreau MC, Olmstead MM, Lord PA, Balch AL (2001) Addition of diprotic nucleophiles to a C60-tetrazine monoadduct: structural reassignment and correction of a novel rearrangement. Chem Comm:1758–1759
Qian W, Chuang S-C, Amador RB, Jarrosson T, Sander M, Pieniazek S, Khan SI, Rubin Y (2003) Synthesis of stable derivatives of C62: the first nonclassical fullerene incorporating a four-membered ring. J Am Chem Soc 125(8):2066–2067
Murata Y, Kato N, Komatsu K (2001) The reaction of fullerene C60 with phthalazine: The mechanochemical solid-state reaction yielding a new C60 dimer versus the liquid-phase reaction affording an open-cage fullerene. J Org Chem 66(22):7235–7239
Murata Y, Murata M, Komatsu K (2001) The reaction of fullerene C60 with 4,6-dimethyl-1,2,3-triazine: Formation of an open-cage fullerene derivative. J Org Chem 66(24):8187–8191
Murata Y, Murata M, Komatsu K (2003) Synthesis, structure, and properties of novel open-cage fullerenes having heteroatom(s) on the rim of the orifice. Chem Eur J 9(7):1600–1609
Lamparth I, Maichle-Mössmer C, Hirsch A (1994) Reversible template-directed activation of equatorial double bonds of the fullerene framework: Regioselective direct synthesis, crystal structure, and aromatic properties of Th-C66(COOEt)12. Angew Chem Int Ed Engl 34(15):1607–1609
Hirsch A, Vostrowsky O (2001) C60 Hexakisadducts with an octahedral addition pattern – A new structure motif in organic chemistry. Eur J Org Chem:829–848
Castro E, Azmani K, Garcia AH, Aghabali A, Liu S, Metta-Magana AJ, Olmstead MM, Rodríguez-Fortea A, Poblet JM, Echegoyen L (2017) Unusual C2h-synnteric trans-1-(bis-pyrrolidine)-tetra-malonate hexa-adducts of C60: The unexpected regio- and stereocontrol mediated by malonate–pyrrolidine interaction. Chem Eur J 23(63):15937–15944
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Yamada, M., Nagase, S., Akasaka, T. (2021). Functionalization of Fullerenes: Addition Reactions. In: Lu, X., Akasaka, T., Slanina, Z. (eds) Handbook of Fullerene Science and Technology. Springer, Singapore. https://doi.org/10.1007/978-981-13-3242-5_33-1
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