Synthesis of Simple Diynals, Diynones, Their Hydrazones, and Diazo Compounds: Precursors to a Family of Dialkynyl Carbenes (R1 C C C̈ C C R2)

NP Bowling, NJ Burrmann, RJ Halter…

Index: Bowling, Nathan P.; Burrmann, Nicola J.; Halter, Robert J.; Hodges, Jonathan A.; McMahon, Robert J. Journal of Organic Chemistry, 2010 , vol. 75, # 19 p. 6382 - 6390

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Citation Number: 24

Abstract

A variety of substituted pentadiynols,-diynals, and-diynones have been prepared en route to precursors to dialkynyl carbenes (R1 C C C̈ C C R2). In light of the marginal stability associated with these simple systems, several strategies were required to assemble the carbon backbones. The requisite five-carbon skeletons were prepared using 4+ 1, 3+ 2, 2+ 2+ 1, and 2+ 1+ 1+ 1 coupling methodologies. The Dess− Martin periodinane serves ...