DOI: 10.1039/A802677G
(Paper)
Reference Section for: J. Chem. Res. (S), 1998, 658-659
Unusual Azetidine or Oxazine Formation upon Reaction of O-Ethyl Dithiocarbonate with 1,2,3-Triphenyl-3-Phthalimidopropyl Iodides; Erythro Selectivity in the Reaction of Iodotrimethylsilane with Phthalimidopropanols
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M. E. Ivanova, V. B. Kurteva, M. J. Lyapova and I. G. Pojarlieff
Abstract
Reaction of isomeric 1,2,3-triphenyl-3-phthalimidopropanols with hexamethyldisilane and iodine gave highly selectively iodides 3 with 1,2-erythro configuration which treated with O-ethyl dithiocarbonate yielded from ET-3 the xanthate ester 4, the trans,trans-dihydrooxazine 5 and the olefin 6 as major products while from EE-3 the cis,trans-azetidine 7 was obtained in 75% yield.
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