Mechanistic aspects of alkyne migration in alkylidene carbenoid rearrangements.

[摘要]：propensity of the alkynyl RCYC- group to migrate in an alkynyl-vinylidene carbenoid intermediate species. Lithiation of R3SiCYCCR1:13CBr2 or R3SiCYC13CR1:CBr2 (R = Me, iPr) was performed for generation of the corresponding a-bromovinyllithium carbenoids, which undergo migration of R3SiCYC or R1 yielding diynes R3SiCYC13CYCR1 and/or R3SiCYCCY13CR1, resp. The migratory ability of the alkynyl groups was evaluated in comparison with aryl, silylethynyl, vinyl and alkyl groups.

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