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 1472-7781Full text not available in this repository. (Request a copy from the Strathclyde author)
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.
|Keywords:||acids, azafulvenium methides, organic chemistry, sulfur dioxide, Pharmacy and materia medica, Chemistry(all)|
|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:||27 Apr 2016 11:23|