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Reaction of 1,2-Di(1-adamantyl)-2-thioxoethanone with Diazomethanes; 1,3- versus 1,5-Dipolar Electrocyclization of a Sterically Crowded Thiocarbonyl S-Methylide

Mlostoń G., Urbaniak K., Nomura T., Nakayama J., Heimgartner H.

Polish Journal of Chemistry

2009

Vol. 83, nr 11

1945-1951

The reaction of 1,2-di(1-adamantyl)-2-thioxoethanone (4c) with diazomethane and 2-diazopropane yielded 2-acylthiiranes 6a and 6b, respectively, and no 1,3-oxathioles of type 7 were formed. The reaction course is explained via [2+3]-cycloaddition, elimination of N2, and 1,3-dipolar electrocyclization of the in ter me di ate acyl-substituted thiocarbonyl ylides of type 1. The fail ure of the competitive 1,5-dipolar electrocyclization is a result of the sterically unfavor able conformation 1a.