Abstract
Bu3SnH-mediated aryl radical cyclisations of a range of N-vinylic 2-iodobenzamides 10 were examined. The enamides 10a–d gave exclusively the 5-exo cyclisation products 11a–d, whereas the enamides 10e,f having a phenyl substituent on the vinylic carbon atom α to the nitrogen atom gave predominantly the 6-endo cyclisation products 14 and 18, respectively. The experiments on the effect of concentration of Bu3SnH or temperature on the products distribution showed that the formation of the 6-endo cyclisation products 14 and 18 was a result of a 5-exo cyclisation of the aryl radicals formed from 10e,f followed by neophyl rearrangement of the intermediate radicals.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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