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Abstract
On 1.2‐Shift Reactions and CH‐Insertions of Acyclic Alkylidene CarbenesTwo series of acyclic terminal vinyl bromides (1…4 and 5…7) were tested in the reaction with potassium tert‐butoxide as precursors of alkylidene carbenes. As expected 1 up to 4 only give 1‐alkynes whereas the 2‐methylated vinyl bromides 5, 6 and 7 yield 1‐methylated cyclopentenes predominantly besides 2‐alkynes. The formation of cyclopentenes indicates a reaction route via alkylidene carbenes and 1,5‐CH‐insertion reactions, that of 2‐alkynes is convincing evidence for 1,2‐alkyl shift reactions in 2‐methyl substituted alkylidene carbenes. The selectivity of 1,5‐CH‐insertion depends on the degree of alkyl substitution of the C‐5‐atom. At 240°C the selectivity is 1°:2°:3° ≈ 1:54:240.
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