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Synthesis 1988; 1988(4): 281-283
DOI: 10.1055/s-1988-27543
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Synthesis of Methyl 5-Aryl-3-oxo-4-pentenoates and Novel Substituted Cyclopentenones

C. V. Asokan* , S. Bhattacharji, H. Ila, H. Junjappa
  • *Department of Chemistry, North-Eastern Hill University, Shillong 793 003, Meghalaya, India
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Publication Date:
20 August 2002 (online)

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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.

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