Srinivasa Rao, Ch. ; Chandrasekharam, M. ; Patro, Balaram ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1994) Facile one pot thermal dehydration and dethioacetalization of β-hydroxydithioacetals with dimethyl sulphoxide: synthesis of α,β-unsaturated aldehydes Tetrahedron, 50 (19). pp. 5783-5794. 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)85646-5
Abstract
The acyclic and cyclic β -hydroxydithioacetals 3a-m and 4a-b obtained by sodium borohydride reduction (or Grignard addition) of the corresponding β -oxodithioacetals 2a-m are shown to undergo facile one pot thermal dehydration and dethioacetalization in the presence of dimethyl sulphoxide to afford the corresponding ene- and polyene aldehydes 5a-m and 6a-b in good yields. The probable mechanism of dethioacetalization with dimethyl sulphoxide has also been discussed.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 24061 |
| Deposited On: | 29 Nov 2010 10:31 |
| Last Modified: | 22 Feb 2011 05:20 |
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