Abstract

Thermal reaction of alkynyl propargyl sulfides 1 in the presence of n-BuN3 followed by moist silica gel treatment afforded 4-methylenecyclobutenones 4 in moderate yields. Photogeneration of allenylketenes 5 from 4 in the presence of amine or methanol gave 3,4-pentadienamides 6 or methyl 3,4-pentadienates 7, respectively. Similar reaction in the presence of aldimines afforded unsaturated δ-lactams 9 in good yields.

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