Journal of the Chemical Society. Perkin transactions I p. 313 - 317 (1996)
Update date:2022-08-11
Topics:
Smith, Gareth
Sparey, Tim J.
Taylor, Paul C.
Reaction of the tosyl imides 6 and 8 of 1,3-dithiane and 1,3,5-trithiane with sodium hydride and alkyl iodides in DMF yields anti alkylated products in all cases. In the case of the trithiane imide 8, both mono- and di-alkylation is observed. Preparation of cyclic sulfimide analogues of Eliel's oxathiane is shown to be problematic, but a new class of O,S-acetals, namely 4-bromophenylthiomethyl (BPTM) ethers, is introduced as a replacement for their troublesome phenylthiomethyl (PTM) analogues.
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