HALOGENATION OF DIAZOPROPANE WITH T-BUTYL HYPOBROMITE . EVIDENCE FOR FORMATION OF ALPHA-BROMOPROPYLIDENE

Reaction of diazopropane and t-butyl hypobromite at -100° and subsequent warming of the reaction mixture to room temperature leads to the formation of cis- and trans-1-bromopropene, 1-bromopropane, 1,1-dibromo-propane, 1,1-dibromopropene, and cis- and (trans-3-bromo-3-hexene. The effect of reaction conditions on the product distribution and other observations have been interpreted on the basis of the formation of α-bromodiazopropane and its thermal or photochemical decomposition to give α-bromopropylidene. © 1969, American Chemical Society. All rights reserved.