December 28, 2024, 04:01:28 AM
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Topic: conversion of 2-allyloxybenzaldoxime to 4H-[1]Benzopyrano[4,3-c]-2-isoxazoline  (Read 3744 times)

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Offline heathcliff

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hey all,

can anybody show me the mechanism for this coversion?

cheers!



 
« Last Edit: April 10, 2008, 11:44:46 AM by heathcliff »

Offline Custos

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How about something like this. A cycloaddition of the deprotonated aldoxime followed by an oxidation step to give the product. Another alternative is the oxidative step first to give a titrile oxide, which will undergo cycloaddition with the allyl group to give the isoxazoline. However, that puts the double bond in the wrong position and would require a double-bond migration, which frankly I think is unlikely.

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