Abstract
The conformational control of the Wolff rearrangement (WR) has been studied by means of a comparative study of the low temperature photolysis of argon-matrix isolated α-diazo ketones, 1, and of vinylene thioxocarbonates, 2. Under these conditions the s-E, s-Z conformational equilibrium of 1 will be hindered whereas 2 has a fixed s-Z conformation. The results indicate that the conformational control observed in the WR of α-diazo ketones is not per se a proof for a concerted mechanism and that a mechanism involving a ketocarbene intermediate is the most reasonable.
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