By Wolfgang Kirmse (Auth.)
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Extra resources for Carbene Chemistry
Formation of , , and methyl chloride most likely proceeds by a polar mechanism, whereas loss of the bridge is radical or concerted in nature. R 1 I c r ^ r I + ( C H sO ) 2C : CI  ( C H 30 ) 2C = C ( O C H 3) 2  Since bridge loss has been shown to be unimolecular (190,192), tetramethoxyethylene probably arises through the dimerization of dimethoxycarbene. In accord with this hypothesis, no tetramethoxyethylene was obtained from the liquid-phase pyrolysis of [53a] under conditions of high dilution, or from the gas-phase pyrolysis of [53c] (192).
VI. BAMFORD-STEVENS REACTION — C - j - C = N — Ν — S 0 2R *~ jjC=C^ 33 -* Κ -Ky/ Η + K > = £ > \ 4 c = ~ H N ) /Η Reduction of tosylhydrazones to saturated hydrocarbons is brought about by lithium aluminum hydride and sodium borohydride (137-141). Aluminum alkoxides are capable of generating diazoalkanes from tosylhydrazones, but subsequently act as Lewis acids to give carbonium ionderived products (142). C. Effect of Structure Even with a proper choice of solvent and base, not all tosylhydrazones can be induced to give carbene intermediates.
The halodiazomethanes undergo thermolysis at —10° or may be photolyzed at —50° (116). Similarly, reaction of 1-diazopropane and i-butyl hypobromite at —100° and subsequent warming of the reaction mixture to — 30° led to the formation of products derived from 1-bromo-1-diazopropane (117). Halogenation of diazomethane with two equivalents of ( 3 1 29 VI. BAMFORD-STEVENS REACTION ί-butyl hypohalites probably leads to dihalodiazomethanes which are too unstable to be characterized and decompose spontaneously even at - 1 0 0 ° (116).
Carbene Chemistry by Wolfgang Kirmse (Auth.)