Synthesis of unsymmetrically substituted 1, 3-butadiynes and 1, 3, 5-hexatriynes via alkylidene carbenoid rearrangements

…, ET Chernick, S Eisler, RR Tykwinski

Index: Shi Shun, Annabelle L. K.; Chernick, Erin T.; Eisler, Sara; Tykwinski, Rik R. Journal of Organic Chemistry, 2003 , vol. 68, # 4 p. 1339 - 1347

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Citation Number: 88

Abstract

Unsymmetrically substituted 1, 3-butadiynes and 1, 3, 5-hexatriynes are synthesized in four steps from commercially available aldehydes or carboxylic acids. The key step in this process involves a Fritsch-Buttenberg-Wiechell rearrangement, in which an alkylidene carbenoid intermediate subsequently rearranges to the desired polyyne. This rearrangement proceeds under mild conditions, and it is tolerant of a range of ...

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