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Absolute rate constants for the ylide-forming reactions of 16 carbenes with pyridine range from 1.4 x 1010 to 1.2 x lo5 dm3 mol-1 s-1, and can be rationalized by frontier molecular orbital theory.

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The 1,2‐carbenic hydride shift of neopentylmethoxycarbene was suppressed by the methoxy substituent. Thermally activated hydride shifts were observed with phenoxymethylmethoxycarbene and phenoxymethyltrifluoro‐ethoxycarbene, where appropriate potentiating substituents were introduced at both the migration origin and the migration terminus. Similarly, the 1,3‐CH insertion reaction of tert‐butylfluorocarbene could be induced by thermal activation.

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