Bhat, Laxminarayan ; Thomas, Abraham ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1992) Attempted Simmons-Smith reaction on α-oxoketene dithioacetals: a new general route to 3,4-substituted and annelated thiophenes Tetrahedron, 48 (47). pp. 10377-10388. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)88342-3
Abstract
A new general synthesis of 3- and 3,4-substituted 4a-q, 3,4-annelated 7a-d and condensed tricyclic 9a-e thiophenes has been developed through Simmons-Smith reaction on the respective α-oxoketene dithioacetals. Extension of the reaction to α-cinnamoylketene dithioacetals 10a-e and its higher enyl analogs 13a-d, 15a-c gave the corresponding 3-styryl 11a-e and 3-di- and trienyl 14a-d, 16a-c thiophenes in highly regioselectivemanner. A probable mechanism involving an unutual intramolecular aldol condensation of sulphonium ylid formed through carbenoid methylene insertion on divalent sulfur has been suggested.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| Keywords: | α-oxoketene Dithioacetals; Simmons-smith Reaction; 3- and 3; 4-substituted Thiophenes; Carbene Insertion Into Sulphur |
| ID Code: | 15289 |
| Deposited On: | 13 Nov 2010 12:59 |
| Last Modified: | 22 Feb 2011 08:40 |
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