Asokan, C. V. ; Bhattacharji, S. ; Ila, H. ; Junjappa, H. (1988) Synthesis of methyl 5-aryl-3-oxo-4-pentenoates and novel substituted cyclopentenones Synthesis, 1988 (4). pp. 281-283. ISSN 0039-7881
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Official URL: https://www.thieme-connect.com/ejournals/abstract/...
Related URL: http://dx.doi.org/10.1055/s-1988-27543
Abstract
The cinnamoyl- (1a-j) and (5-phenyl-2,4-pentadienoyl)- (1k) ketene dithioacetals are shown to undergo methanolysis in the presence of ether-boron trifluoride complex and mercury(II) chloride to the corresponding methyl 5-aryl-3-oxo-4-pentenoates 2a-j and 3-oxo-7-phenyl- 4,6-heptadienoate (2k), respectively, in good yields. However, the corresponding (2-methylcinnamoyl)ketene dithioacetals 3a-f, under identical reaction conditions, undergo Nazarov cyclization to give the corresponding substituted cyclopentenones 4a-f.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Thieme Medical Publishers Inc. |
| ID Code: | 15346 |
| Deposited On: | 13 Nov 2010 09:30 |
| Last Modified: | 03 Jun 2011 06:26 |
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