The Journal of Organic Chemistry

Cyanoketenes. Cycloadditions of chlorocyanoketene to alkynes. Generation of vinylogous cyanoketenes

PL Fishbein, HW Moore

Index: Fishbein, Paul L.; Moore, Harold W. Journal of Organic Chemistry, 1985 , vol. 50, # 17 p. 3226 - 3228

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Citation Number: 12

Abstract

Chlorocyanoketene (CCK), an exceptionally reactive electrophilic ketene, has previously been shown to undergo facile cycloadditions to imines,'formimidates, 2 aryl aldehyde~,~ s~ lfurdimides,~ and alkenes. 5 Its ability to cycloadd to selected alkynes is reported in this manuscript. Also reported is the observation that the resulting cyclobutenones function as precursors to vinylketenes. Indeed, the 4-chloro-4-cyanocyclobutenones arising from the ...