Synthesis of Heterasumanene

Abstract

This article outlines the efforts toward the synthesis of heterasumanene, a buckybowl consisting of four six-membered and three five-membered rings. Special attention is paid to our achievement on the facile and large-scale synthesis of trithia- and triselenasumanenes.

Key words

polycycles - buckybowls - sulfur - selenium - silicon

• References

• 1 Pérez EM, Martín N. Chem. Soc. Rev. 2008; 37: 1512
• 2 Kroto HW, Heath JR, O’Brien SC, Curl RF, Smalley RE. Nature (London, U.K.) 1985; 318: 162

For comprehensive reviews, see:
• 3a Rabideau PW, Sygula A. Acc. Chem. Res. 1996; 29: 235
• 3b Wu Y.-T, Siegel JS. Chem. Rev. 2006; 106: 4843
• 3c Tsefrikas VM, Scott LT. Chem. Rev. 2006; 106: 4868
• 3d Amaya T, Hirao T. Chem. Commun. 2011; 47: 10524
• 4 Sakurai H, Daiko T, Hirao T. Science 2003; 301: 1878
• 5a Sakurai H, Daiko T, Sakane H, Ayama T, Hirao T. J. Am. Chem. Soc. 2005; 127: 11580
• 5b Amaya T, Sakane H, Hirao T. Angew. Chem. Int. Ed. 2007; 46: 8376
• 5c Ayama T, Mori K, Wu H.-L, Ishida S, Nakamura J, Murata K, Hirao T. Chem. Commun. 2007; 1902
• 5d Ayama T, Nakata T, Hirao T. J. Am. Chem. Soc. 2009; 131: 10810
• 5e Amaya T, Wang W.-Z, Sakane H, Moriuchi T, Hirao T. Angew. Chem. Int. Ed. 2010; 49: 403
• 5f Amaya T, Seki S, Moriuchi T, Nakamoto K, Nakata T, Sakane H, Saeki A, Tagawa S, Hirao T. J. Am. Chem. Soc. 2009; 131: 408
• 5g Higashibayashi S, Tsuruoka R, Soujanya Y, Purushotham U, Sastry GN, Seki S, Ishikawa T, Toyota S, Sakurai H. Bull. Chem. Soc. Jpn. 2012; 85: 450
• 6 Tan Q.-T, Higashibayashi S, Karanjit S, Sakurai H. Nat. Commun. 2012; 3: 891
• 7a Imamura K, Takimiya K, Aso Y, Otsubo T. Chem. Commun. 1999; 1859
• 7b Furukawa S, Kobayashi J, Kawashima T. J. Am. Chem. Soc. 2009; 131: 14192
• 7c Saito M, Tanikawa T, Tajima T, Guo J, Nagase S. Tetrahedron Lett. 2010; 51: 672
• 7d Furukawa S, Kobayashi J, Kawashima T. Dalton Trans. 2010; 39: 9329
• 7e Tanikawa T, Saito M, Guo J, Nagase S. Org. Biomol. Chem. 2011; 9: 1731
• 7f Higashibayashi S, Sakurai H. Chem. Lett. 2011; 40: 122
• 7g Tanikawa T, Saito M, Guo J, Nagase S, Minoura M. Eur. J. Org. Chem. 2012; 36: 7135
• 8a Priyakumar UD, Sastry GN. Tetrahedron Lett. 2001; 42: 1379
• 8b Priyakumar UD, Sastry GN. J. Org. Chem. 2001; 66: 6523
• 8c Sastry GN, Priyakumar UD. J. Chem. Soc., Perkin Trans. 2 2001; 30
• 9a Klemm LH, Hall E, Cousins L, Klopfensitein CE. J. Heterocycl. Chem. 1987; 24: 1749
• 9b Klemm LH, Hall E, Cousins L, Klopfensitein CE. J. Heterocycl. Chem. 1989; 26: 345
• 10a Ashe AJ. III, Kampf JW, Savla PM. Heteroat. Chem. 1994; 5: 113
• 10b Ashe AJ. III, Kampf JW, Savla PM. J. Org. Chem. 1990; 55: 5558
• 11a Schroth W, Hintzsche E, Chem D, Felicetti M, Spitzner HR, Sieler J, Kempe R. Angew. Chem., Int. Ed. Engl. 1994; 33: 739
• 11b Okamoto T, Kudoh K, Wakamiya A, Yamaguchi S. Org. Lett. 2005; 7: 5301
• 11c Jiang W, Zhou Y, Geng H, Jiang S, Yan S, Hu W, Wang Z, Shuai Z, Pei J. J. Am. Chem. Soc. 2011; 133: 1
• 12 Kobayashi J, Furukawa S, Shirokawa M, Kawashima T. Abstract of 4th Asian Silicon Symposium in Tsukuba 2012; 140
• 13 Li X, Zhu Y, Shao J, Wang B, Zhang S, Shao Y, Jin X, Yao X, Fang R, Shao X. Angew. Chem. Int. Ed. 2014; 53: 535
• 14a Boden N, Borner RC, Bushby RJ, Cammidge AN, Jesudason MV. Liq. Cryst. 1993; 15: 851
• 14b Kumar S, Varshney SK. Liq. Cryst. 1999; 26: 1841
• 14c Mahoney SJ, Ahmida MM, Kayal H, Fox N, Shimizu Y, Eichhorn SH. J. Mater. Chem. 2009; 19: 9221