Bhat, Laxminarayan ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1994) Rearrangement studies on acylketene O-prop-2-ynyl S-methylmonothioketals Journal of the Chemical Society, Perkin Transactions 1, 1 (13). pp. 1749-1752. ISSN 0300-922X
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1994...
Related URL: http://dx.doi.org/10.1039/P19940001749
Abstract
Acylketene O-prop-2-ynyl S-methylmonothioketals 3a-e, easily obtained through displacement on β-oxosulfonium salts 2a-e by prop-2-ynol, are shown to undergo facile rearrangement under neutral (toluene-xylene) and basic conditions (K2CO3-EtCOMe) to afford the diene esters 5a-e and the substituted furans 4a-e, respectively. The probable mechanism for the formation of the various products involving initial Claisen rearrangement of compounds 3a-e has been described.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 15444 |
| Deposited On: | 13 Nov 2010 08:50 |
| Last Modified: | 22 Feb 2011 08:33 |
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