STERIC AND ELECTRONIC EFFECTS IN IMINE-HEMIAMINAL RING-CHAIN TAUTOMERISM

Authors
DERRICK SD BOEHME R WONG KM NEMETH F TANAKA K RUMBERG B BEEKMAN RA DIBBLE PW
Citation
Sd. Derrick et al., STERIC AND ELECTRONIC EFFECTS IN IMINE-HEMIAMINAL RING-CHAIN TAUTOMERISM, Tetrahedron, 52(22), 1996, pp. 7679-7690
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
22
Year of publication
1996
Pages
7679 - 7690
Database
ISI
SICI code
0040-4020(1996)52:22<7679:SAEEII>2.0.ZU;2-E
Abstract
We have examined a series of 1,3-dihydro-1-dihydro-1-isobenzofuranamin es that exist in an imine/hemiaminal ring-chain tautomerism. The tauto meric free energies are rationalized in terms of electronic and steric effects. A series of compounds bearing substituents of varying bulk h ave free energies that correlate well with substituent A values. Copyr ight (C) 1996 Elsevier Science Ltd