Picture of a sphere with binary code

Making Strathclyde research discoverable to the world...

The Strathprints institutional repository is a digital archive of University of Strathclyde research outputs. It exposes Strathclyde's world leading Open Access research to many of the world's leading resource discovery tools, and from there onto the screens of researchers around the world.

Explore Strathclyde Open Access research content

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

Full text not available in this repository. (Request a copy from the Strathclyde author)

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.