REACTIONS OF 1-AZA-3-ETHYLBICYCLO[1.1.0]BUTANE WITH ELECTROPHILES - A FACILE ENTRY INTO NEW, N-SUBSTITUTED 3-ETHYLIDENEAZETIDINES AND 2-AZETINES

被引：48

作者：

MARCHAND, AP ^{[1
]}

RAJAGOPAL, D ^{[1
]}

BOTT, SG ^{[1
]}

ARCHIBALD, TG ^{[1
]}

机构：

[1] AEROJET,DIV PROP,SACRAMENTO,CA 95813

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 07期

关键词：

D O I：

10.1021/jo00086a008

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 1-aza-3-ethylbicyclo [1.1.0]butane (3) with N2O4 under a variety of experimental conditions afforded several products, 4-7, all of which resulted via addition across the strained central C(3)-N sigma-bond in 3. The corresponding reactions of ClCO(2)Et, Tf(2)O, and Ms(2)O with 3 also have been studied. These reactions provide useful methods for synthesizing N-substituted 3-ethylideneazetidines and 2-azetines.

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页码：1608 / 1612

页数：5

相关论文

共 29 条

[1] SYNTHESIS OF POLYNITROCYCLOBUTANE DERIVATIVES [J].

ARCHIBALD, TG ;

GARVER, LC ;

BAUM, K ;

COHEN, MC .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2869-2873

[2] SYNTHESIS AND X-RAY CRYSTAL-STRUCTURE OF 1,3,3-TRINITROAZETIDINE [J].

ARCHIBALD, TG ;

GILARDI, R ;

BAUM, K ;

GEORGE, C .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2920-2924

[3] SYNTHESIS OF 1,3,3-TRINITROAZETIDINE [J].

AXENROD, T ;

WATNICK, C ;

YAZDEKHASTI, H ;

DAVE, PR .

TETRAHEDRON LETTERS, 1993, 34 (42) :6677-6680

[4] SIR88 - A DIRECT-METHODS PROGRAM FOR THE AUTOMATIC SOLUTION OF CRYSTAL-STRUCTURES [J].

BURLA, MC ;

CAMALLI, M ;

CASCARANO, G ;

GIACOVAZZO, C ;

POLIDORI, G ;

SPAGNA, R ;

VITERBO, D .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :389-393

[5]

COREY EJ, 1975, TETRAHEDRON LETT, P3117

[6]

Cromer D.T, 1974, INT TABLES XRAY CRYS, VIV

[7] AZETIDINES - RECENT SYNTHETIC DEVELOPMENTS [J].

CROMWELL, NH .

CHEMICAL REVIEWS, 1979, 79 (04) :331-358

[8]

CROMWELL NH, 1976, J HETEROCYCLIC CHEM, V13, pS1

[9] THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].

DEWAR, MJS ;

ZOEBISCH, EG ;

HEALY, EF ;

STEWART, JJP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909

[10] SYNTHESES AND REACTIONS OF 1-AZABICYCLO(1.1.0)BUTANES [J].

FUNKE, W .

CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (09) :3148-&