Reaction of Allenamides with [60]Fullerene: Formation of Novel Cyclobutane Annulated Fullerene Derivatives

Vijay  Nair; Divakaramenon  Sethumadhavan; Smitha M.  Nair; Ponnusamy  Shanmugam; Palathingal M.  Treesa; Guenter K.  Eigendorf

doi:10.1055/s-2002-33638

SHORTPAPER

Reaction of Allenamides with [60]Fullerene: Formation of Novel Cyclobutane Annulated Fullerene Derivatives

Vijay Nair*^a, Divakaramenon Sethumadhavan^a, Smitha M. Nair^a, Ponnusamy Shanmugam^a, Palathingal M. Treesa^a, Guenter K. Eigendorf^b
^a Organic Chemistry Division, Regional Research Laboratory, CSIR, Trivandrum 695 019, India
Fax: 91(471)491712; e-Mail: gvn@csrrltrd.ren.nic.in;
^b Department of Chemistry, The University of British Columbia, Vancouver, V6T 1Z1, Canada

Abstract

Alle Artikel dieser Rubrik

Abstract

Reaction of allenamides with [60]fullerene afforded novel cyclobutane annulated fullerene derivatives. Cyclobutanation utilizing the C1′-C2′ double bond of allenamides with [60]fullerene was observed.

Key words

allenes - cyclizations - fullerenes - annulations - cyclobutanes - allenamides

Volltext

Referenzen

References

<A NAME="RZ01202SS-1A">1a</A> Kroto HW. Heath JR. O" Brien SC. Curl RF. Smalley RE. Nature (London) 1985, 318: 162

<A NAME="RZ01202SS-1B">1b</A> Krätschmer W. Lamb LD. Fostiropoulos K. Huffman DR. Nature (London) 1990, 347: 354

<A NAME="RZ01202SS-2A">2a</A> Segura JL. Martin N. Chem. Rev. 1999, 99: 3199

<A NAME="RZ01202SS-2B">2b</A> Sliwa W. Fullerene Sci. Technol. 1997, 5: 1133

<A NAME="RZ01202SS-2C">2c</A> Hirsch A. Synthesis 1995, 895

<A NAME="RZ01202SS-3A">3a</A> Prato M. Maggini M. Acc. Chem. Res. 1998, 31: 519

<A NAME="RZ01202SS-3B">3b</A> Nair V. Sethumadhavan D. Sheela KC. Eigendorf GK. Tetrahedron Lett. 1999, 40: 5087

<A NAME="RZ01202SS-4A">4a</A> Hirsch A. Lamparth IS. Grosser T. Karfunkel HR. J. Am. Chem. Soc. 1994, 116: 9385

<A NAME="RZ01202SS-4B">4b</A> Echegoyen LE. Djojo FD. Hirsch A. Echegoyen L. J. Org. Chem. 2000, 65: 4994

<A NAME="RZ01202SS-4C">4c</A> Diederich F. Thilgen C. Science 1996, 271: 317

<A NAME="RZ01202SS-4D">4d</A> Diederich F. Kessinger R. Acc. Chem. Res. 1999, 32: 537

<A NAME="RZ01202SS-5A">5a</A> Vassilikogiannakis G. Hatzimarinaki M. Orfanopoulos M. J. Org. Chem. 2000, 65: 8180

<A NAME="RZ01202SS-5B">5b</A> Wilson SR. Kaprinidis N. Wu Y. Schuster DI. J. Am. Chem. Soc. 1993, 115: 8495

<A NAME="RZ01202SS-5C">5c</A> Zhang X. Romero A. Foote CS. J. Am. Chem. Soc. 1993, 115: 11024

<A NAME="RZ01202SS-5D">5d</A> Yamago S. Takeichi A. Nakamura E. J. Am. Chem. Soc. 1994, 116: 1123

<A NAME="RZ01202SS-5E">5e</A> Matsui S. Kinbara K. Saigo K. Tetrahedron Lett. 1999, 40: 899

<A NAME="RZ01202SS-5F">5f</A> Prato M. Maggini M. Scorrano G. Lucchini V. J. Org. Chem. 1993, 58: 3613

<A NAME="RZ01202SS-5G">5g</A> Hoke SHII. Molstad J. Dilettato D. Jay MJ. Carlson D. Kahr B. Cooks RG. J. Org. Chem. 1992, 57: 5069

<A NAME="RZ01202SS-6A">6a</A> Wang G.-W. Komastu K. Murata Y. Shiro M. Nature (London) 1997, 387: 583

<A NAME="RZ01202SS-6B">6b</A> Komastu K. Wang G.-W. Murata Y. Tanaka T. Fujiwara KJ. Org. Chem. 1998, 63: 9358

<A NAME="RZ01202SS-7">7</A> Shu LH. Sun WQ. Zang DW. Wu SH. Wu HM. Xu JF. Lao XF. Chem. Commun. 1997, 79

<A NAME="RZ01202SS-8A">8a</A> Broggin G. Brucheand L. Zecchi G. J. Chem. Soc., Perkin Trans. 1 1990, 533

<A NAME="RZ01202SS-8B">8b</A> Wei L.-L. Xiong H. Douglas CJ. Hsung RP. Tetrahedron Lett. 1999, 40: 6903

<A NAME="RZ01202SS-9">9</A> Kimura M. Horino Y. Wakamiya Y. Okajima T. Tamaru Y. J. Am. Chem. Soc. 1997, 119: 10869

<A NAME="RZ01202SS-10A">10a</A> Wei L.-L. Hsung RP. Xiong H. Mulder JA. Nkansah NT. Org. Lett. 1999, 1: 2145

<A NAME="RZ01202SS-10B">10b</A> Kimura M. Wakamiya Y. Horino Y. Tamaru Y. Tetrahedron Lett. 1997, 38: 3963

<A NAME="RZ01202SS-11A">11a</A> Bingel C. Chem. Ber. 1993, 126: 1957

<A NAME="RZ01202SS-11B">11b</A> Camps X. Hirsch A. J. Chem. Soc., Perkin Trans. 1 1997, 1595 ; and references cited therein