Azafulvenium methides: new extended dipolar systems

Sutcliffe, O.B. and Storr, R.C. and Gilchrist, T.L. and Rafferty, P. (2001) Azafulvenium methides: new extended dipolar systems. Journal of the Chemical Society, Perkin Transactions 1, 2001 (15). pp. 1759-1806. ISSN 1472-7781 (http://dx.doi.org/10.1039/b103250j)

Abstract

The transient 1-azafulvenium methides 24, 26 and 28 generated by thermal extrusion of sulfur dioxide from pyrrolo[1,2-c][1,3]thiazole 2,2-dioxide 20 (R = Me), 22 and 23 undergo sigmatropic [1,8]H shifts and the 1-acyl derivatives 30 electrocyclise to give novel pyrrolo[1,2-c][1,3]oxazines 32. The analogous 1,2-diazafulvenium methide 36 has been intercepted in [8 + 2] cycloadditions with electron-rich silylated acetylenes to give adducts 37-40. This behaviour is partially explained by Frontier MO theory.

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• Item metadata

  Item type:	Article
  ID code:	4939
  Dates:	Date Event 2001 Published
  Subjects:	Medicine > Pharmacy and materia medica
  Department:	Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences
  Depositing user:	Strathprints Administrator
  Date deposited:	06 Dec 2007
  Last modified:	08 Apr 2024 15:44
  Related URLs:	http://www.rsc.org/ej/P1/2001/b103250j.p...
  URI:	https://strathprints.strath.ac.uk/id/eprint/4939