Bamford-Stevens reaction – decomposition of diazo intermediate

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Upon heating the diazo compound it decomposes to give the alkene and N₂. In aprotic solvents the decomposition goes via a carbene (Scheme 1) giving predominantly Z-alkenes, whereas in protic solvents the decomposition goes via a carbocation giving a mixture of Z- and E-alkenes (Scheme 2).

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Z. Zhang and J. Wang, Tetrahedron, 2008, 64, 6577–6605.