Torquoselectivity induced by lone-pair conjugation in the electrocyclic reactions of 1-azapolyenes

被引：37

作者：

Walker, MJ ^{[1
]}

Hietbrink, BN ^{[1
]}

Thomas, BE ^{[1
]}

Nakamura, K ^{[1
]}

Kallel, EA ^{[1
]}

Houk, KN ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 20期

关键词：

D O I：

10.1021/jo010466f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Torquoselectivity in the electrocyclic interconversions of 1-azapolyenes. and their heterocyclic isomers was investigated theoretically. The ring openings of 1,2-dihydroazete, 1,2-dihydropyridine, and 1,2-dihydroazocine were examined using HF, MP2, and B3LYP calculations. A large preference for inward rotation of the nitrogen lone pair and outward rotation of the N-H group was found for the four- and six-electron. systems. No strong preference was observed for the eight-electron system.

引用

页码：6669 / 6672

页数：4

共 66 条

[1] ROTATIONAL ENERGY SURFACES OF AZA-1,3-BUTADIENES AND PHOSPHA-1,3-BUTADIENES - A THEORETICAL-STUDY [J].

BACHRACH, SM ;

LIU, MX .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :7929-7937

[2] ABINITIO STUDY OF THE CONROTATORY RING-OPENING OF PHOSPHACYCLOBUTENES AND AZACYCLOBUTENES .1. MONOPHOSPHACYCLOBUTENES AND MONOAZACYCLOBUTENES [J].

BACHRACH, SM ;

LIU, MX .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :209-215

[3] ABINITIO STUDY OF THE CONROTATORY RING-OPENING OF PHOSPHACYCLOBUTENES AND AZACYCLOBUTENES .2. DIPHOSPHACYCLOBUTENES AND DIAZACYCLOBUTENES [J].

BACHRACH, SM ;

LIU, MX .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07) :2040-2047

[4] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[5] DENSITY-FUNCTIONAL THERMOCHEMISTRY .3. THE ROLE OF EXACT EXCHANGE [J].

BECKE, AD .

JOURNAL OF CHEMICAL PHYSICS, 1993, 98 (07) :5648-5652

[6] COMPACT CONTRACTED BASIS-SETS FOR 3RD-ROW ATOMS - GA-KR [J].

BINNING, RC ;

CURTISS, LA .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (10) :1206-1216

[7] DETERMINING ATOM-CENTERED MONOPOLES FROM MOLECULAR ELECTROSTATIC POTENTIALS - THE NEED FOR HIGH SAMPLING DENSITY IN FORMAMIDE CONFORMATIONAL-ANALYSIS [J].

BRENEMAN, CM ;

WIBERG, KB .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1990, 11 (03) :361-373

[8] ATOMIC CHARGES DERIVED FROM ELECTROSTATIC POTENTIALS - A DETAILED STUDY [J].

CHIRLIAN, LE ;

FRANCL, MM .

JOURNAL OF COMPUTATIONAL CHEMISTRY, 1987, 8 (06) :894-905

[9] CHIRAL CONTROL IN THE STAUDINGER REACTION BETWEEN KETENES AND IMINES - A THEORETICAL SCF-MO STUDY ON ASYMMETRIC TORQUOSELECTIVITY [J].

COSSIO, FP ;

ARRIETA, A ;

LECEA, B ;

UGALDE, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) :2085-2093

[10] ON THE THERMAL-BEHAVIOR OF SCHIFF-BASES OF RETINAL AND ITS ANALOGS - 1,2-DIHYDROPYRIDINE FORMATION VIA 6-PI-ELECTRON ELECTROCYCLIZATION OF 13-CIS ISOMERS [J].

DELERA, AR ;

REISCHL, W ;

OKAMURA, WH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (11) :4051-4063

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