Transition states of the retro-ene reactions of allylic diazenes

被引：16

作者：

Jabbari, Arash

Sorensen, Erik J.

Houk, K. N. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

[2] Princeton Univ, Dept Chem, Princeton, NJ 08544 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 14期

关键词：

D O I：

10.1021/ol0612049

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Density functional theory studies of intramolecular retro-ene reactions of allyldiazenes show that the reaction is a concerted process involving a six-center cyclic transition state. The activation barriers for deazetization for X = H, Me, F, Cl, and Br (3a-e) are 2.4, 40.2, 22.3, 9.3, and 8.8 kcal/mol, respectively.

引用

页码：3105 / 3107

页数：3

共 50 条

[1] Retro-ene type fragmentation of allylic dithiolcarbonates
Eto, M
Nishimoto, M
Kubota, S
Matsuoka, T
Harano, K
TETRAHEDRON LETTERS, 1996, 37 (14) : 2445 - 2448
[2] DESULFINATION OF ALLYLIC SULFINIC ACIDS - CHARACTERIZATION OF A RETRO-ENE TRANSITION-STATE
HISCOCK, SD
ISAACS, NS
KING, MD
SUE, RE
WHITE, RH
YOUNG, DJ
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (22): : 7166 - 7169
[3] STEREOCHEMICAL REQUIREMENTS OF ACETYLENIC RETRO-ENE TRANSITION-STATES
VIOLA, A
COLLINS, JJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (24) : 1247 - 1248
[4] Retro-ene reactions in acylallene derivatives
Bibas, H
Koch, R
Wentrup, C
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (08): : 2619 - 2626
[5] Retro-Ene Reactions in Acylallene Derivatives
Bibas, H.
Koch, R.
Wentrup, C.
Journal of Organic Chemistry, 63 (08):
[6] Flavins as enophiles in ene reactions and catalysts for retro-ene reactions
Jensen, Anton
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
[7] THERMAL-DECOMPOSITION OF ALLYLIC SULFINIC ACIDS - A STUDY OF A RETRO-ENE TRANSITION-STATE
HISCOCK, SD
ISAACS, NS
KING, MD
YOUNG, DJ
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (11) : 1381 - 1382
[8] DIRECT OBSERVATION AND RETRO-ENE REACTION OF A PROPARGYLIC DIAZENE - STEREOCHEMICAL ASSIGNMENT OF MONOALKYL DIAZENES
MYERS, AG
FINNEY, NS
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) : 9641 - 9643
[9] ENE AND RETRO-ENE REACTIONS IN GROUP-14 ORGANOMETALLIC CHEMISTRY
DUBAC, J
LAPORTERIE, A
CHEMICAL REVIEWS, 1987, 87 (02) : 319 - 334
[10] Stereoselective allylic reduction via one-pot palladium-catalyzed allylic sulfonation and sulfinyl retro-ene reactions
Um, Hyun-Suk
Min, Jungki
An, Taeyang
Choi, Jin
Lee, Chulbom
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (14): : 2158 - 2162

← 1 2 3 4 5 →