INTRAMOLECULAR S-N(2) RING-OPENING OF CYCLIC SULFATES - 6-EXO-TET VERSUS 7-ENDO-TET CYCLIZATION

Authors
LOHRAY BB RAO BS BASKARAN S VENKATESWARLU S BHUSHAN V
Citation
Bb. Lohray et al., INTRAMOLECULAR S-N(2) RING-OPENING OF CYCLIC SULFATES - 6-EXO-TET VERSUS 7-ENDO-TET CYCLIZATION, Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry, 37(3), 1998, pp. 209-218
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Indian journal of chemistry. Sect. B: organic chemistry, including medical chemistry → ACNP
ISSN journal
03764699
Volume
37
Issue
3
Year of publication
1998
Pages
209 - 218
Database
ISI
SICI code
0376-4699(1998)37:3<209:ISROCS>2.0.ZU;2-X
Abstract
Intramolecular S-N(2) ring opening of trans-cyclic sulfate by in situ generated carboxylate ion, 5-carbon away from the reaction centre, res ults in preferably 6-exo-tet-cyclization whereas cis-cyclic sulfate gi ves a mixture of six- and seven-membered lactones. In contrast, when t he carboxylate ion is situated six carbon atoms away from the reactive cyclic sulfate centre, no intramolecular cyclization is observed.