The oxime ethers 2a-e have been cyclised with Bu,SnH to the alkoxyamino-3-methylidenechromanes 3a-e. Seven-membered ring formation was observed when the oxime ethers 7a. b were converted into the dibenzo[b,e]oxepines 8a. b under similar conditions. 1 -Methoxyaminoindanes 12a. b were produced from the cyclisation of the substrates I l a , b and the cis-fused cyclic products 15a, b and 18 were obtained from compounds 14a. b and 17, respectively.The construction of carbocyclic rings using intramolecular radical cyclisation has become a common strategy in organic synthesis. The first example of the intramolecular trapping of a radical by an oxime ether was reported by Corey and Pyne in 1983.2 The particular advantage of using an oxime ether seems to ! i F in the extra stability of the alkoxy aminyl radicalPaper 410289 1 K
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