Bhat, Laxminarayan ; Thomas, Abraham ; Ila, Hiriyakkanavar ; Junjappa, Hiriyakkanavar (1991) Studies on lead tetraacetate oxidation of α-oxoketene dithioacetals Tetrahedron Letters, 47 (2). pp. 305-312. ISSN 0040-4039
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)80925-X
Abstract
Lead Tetraacetate oxidation of acyclic a-acylketene dithioacetals 1 in refluxing benzene affords α-acetoxyketene dithioacetals 2 as major products which could be hydrolyzed to α-diketone dithioacetals 4 under mild alkaline conditions. Under similar oxidative conditions, α-cinnamoyl ketene dithioacetals 8 yield 2-acetoxycyclopentenone derivatives 9 through an interesting oxidative Nazarov cyclization involving intermediate α-acetoxy dithioacetals accompanied with 1,2-acyl group migration.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 24075 |
| Deposited On: | 29 Nov 2010 10:29 |
| Last Modified: | 22 Feb 2011 05:13 |
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