Intramolecular SN2 ring opening of cyclic sulfate: 6-exo-tet versus 7-exo-tet cyclization

Lohray, Branj. B. ; Rao, Srinivasa B. ; Baskaran, S. ; Venkateshwarlu, S. ; Bhushan, V. (1998) Intramolecular SN2 ring opening of cyclic sulfate: 6-exo-tet versus 7-exo-tet cyclization Indian Journal of Chemistry, 37B . pp. 209-218. ISSN 0019-5103

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Abstract

Intramolecular SN2 ring opening of trans-cyclic sulfate by in situ generated carboxylate ion, 5-carbon away from the reaction centre, results in preferably 6-exo-tet-cyclization whereas cis-cyclic sulfate gives a mixture of six- and seven-membered lactones. In contrast, when the carboxylate ion is situated six carbon atoms away from the reactive cyclic sulfate centre, no intramolecular cyclization is observed.

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Deposited On:01 Oct 2014 06:49
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