Tosyl hydrazones adjacent to epoxides can undergo the Eschenmoser Fragmentation, like this reaction of 16 to give
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Question:
Tosyl hydrazones adjacent to epoxides can undergo the Eschenmoser Fragmentation, like this reaction of 16 to give the unsaturated carbonyl compound 17. The mechanism of this reaction is closely related to the Shapiro reaction.
i. Redraw compound 16 in your answer book and indicate clearly which bonds will be broken in step (e). (2 marks)
ii. Apply your understanding of the Shapiro reaction to propose a mechanism for step (e) under basic conditions (i.e. treatment with BuLi, as in step (a) above). (3 marks)
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