Bamford-Stevens reaction

Step 2

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Sn2

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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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