ELECTROPHILIC AROMATIC REACTIVITIES VIA RING CHAIN TAUTOMERISM OF TETRAHYDRO-1,3-OXAZINES AND 1,3-OXAZOLIDINES

被引：25
|
作者：
FULOP, F [1 ]
DAHLQVIST, M [1 ]
PIHLAJA, K [1 ]
机构：
[1] ALBERT SZENT GYORGYI MED UNIV,INST PHARMACEUT CHEM,H-6701 SZEGED,HUNGARY
来源：
ACTA CHEMICA SCANDINAVICA | 1991年 / 45卷 / 03期
关键词：
D O I：
10.3891/acta.chem.scand.45-0273
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Brown's electrophilic sigma+-constants have been estimated for 2-, 3- and 4-pyridyl substituents with the aid of the ring-chain tautomeric equilibria of several sets of 2-aryl substituted 1,3-oxazolidines and 1,3-oxazines at ambient temperature. The sigma+-values so obtained were best comparable to those determined earlier by solvolytic methods except that for 2-pyridyl which was approximately double. This deviation is due to extra stabilization of the ring from (by ca. 2-3 kJ mol-1) caused by intramolecular hydrogen bonding as indicated by FT-IR measurements.
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收藏
页码：273 / 275
页数：3
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