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)Official URL: 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.
| Item type: | Article |
|---|---|
| ID code: | 4939 |
| Keywords: | acids, azafulvenium methides, organic chemistry, sulfur dioxide, Pharmacy and materia medica |
| Subjects: | Medicine > Pharmacy and materia medica |
| Department: | Faculty of Science > Strathclyde Institute of Pharmacy and Biomedical Sciences |
| Related URLs: | |
| Depositing user: | Strathprints Administrator |
| Date Deposited: | 06 Dec 2007 |
| Last modified: | 04 Oct 2012 12:02 |
| URI: | http://strathprints.strath.ac.uk/id/eprint/4939 |
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