Steric and electronic effects in imine-hemiaminal ring-chain tautomerism

被引：7

作者：

Derrick, SD ^{[1
]}

Boehme, R ^{[1
]}

Wong, KM ^{[1
]}

Nemeth, F ^{[1
]}

Tanaka, K ^{[1
]}

Rumberg, B ^{[1
]}

Beekman, RA ^{[1
]}

Dibble, PW ^{[1
]}

机构：

[1] UNIV LETHBRIDGE, DEPT CHEM, LETHBRIDGE, AB T1K 3M4, CANADA

来源：

TETRAHEDRON | 1996年 / 52卷 / 22期

关键词：

D O I：

10.1016/S0040-4020(96)00352-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We have examined a series of 1,3-dihydro-1-dihydro-1-isobenzofuranamines that exist in an imine/hemiaminal ring-chain tautomerism. The tautomeric free energies are rationalized in terms of electronic and steric effects. A series of compounds bearing substituents of varying bulk have free energies that correlate well with substituent A values. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：7679 / 7690

页数：12

共 31 条

[1] ANATOMY OF A 3 SPECIES TAUTOMERIC PROCESS - THE RING-CHAIN TAUTOMERISM IN 5,6-DIHYDRO-2-HYDROXY-2,3-DIMETHYL-2H-1,4-OXAZINE
ALCAIDE, B
RUBIO, RG
PLUMET, J
RODRIGUEZCAMPOS, IM
[J]. TETRAHEDRON LETTERS, 1990, 31 (29) : 4211 - 4214
[2] HYDROXY SCHIFF BASE-OXAZOLIDINE TAUTOMERISM - APPARENT BREAKDOWN OF BALDWIN RULES
ASTUDILLO, MEA
CHOKOTHO, NCJ
JARVIS, TC
JOHNSON, CD
LEWIS, CC
MCDONNELL, PD
[J]. TETRAHEDRON, 1985, 41 (24) : 5919 - 5928
[3] VAN DER WAALS VOLUMES + RADII
BONDI, A
[J]. JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) : 441 - +
[4] STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM
BOTT, G
FIELD, LD
STERNHELL, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) : 5618 - 5626
[5] RING CHAIN TAUTOMERISM .7. SUBSTITUTED BENZYL-2-CARBOXYLIC AND 2-PHENYLACETYLBENZOIC ACIDS AND THEIR METHYL-ESTERS
BOWDEN, K
MALIK, FP
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (04): : 635 - 639
[6] NATURE OF ORTHO EFFECT .2. COMPOSITION OF TAFT STERIC PARAMETERS
CHARTON, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (03) : 615 - &
[7] BENZO[E]ISOBENZOFURAN - FORMATION AND REACTIONS OF THE PARENT AND ALKOXY-SUBSTITUTED DERIVATIVES
CORNEJO, JJ
GHODSI, S
JOHNSON, RD
WOODLING, R
RICKBORN, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) : 3869 - 3876
[8] Eliel E.L., 1994, Stereochemistry of Organic Compounds
[9] STERIC INTERACTIONS IN ORGANIC-CHEMISTRY - SPATIAL REQUIREMENTS OF SUBSTITUENTS
FORSTER, H
VOGTLE, F
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1977, 16 (07): : 429 - 441
[10] RING-CHAIN TAUTOMERISM OF 1,3-OXAZOLIDINES PREPARED FROM NOREPHEDRINE AND NORPSEUDOEPHEDRINE
FULOP, F
BERNATH, G
MATTINEN, J
PIHLAJA, K
[J]. TETRAHEDRON, 1989, 45 (13) : 4317 - 4324

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