AM1 study of Wolff and 1,2-hydrogen shift rearrangements of beta-oxy-alpha-Diazo carbonyl compounds

被引：5

作者：

Enriquez, F ^{[1
]}

LopezHerrera, FJ ^{[1
]}

Quirante, JJ ^{[1
]}

Sarabia, F ^{[1
]}

机构：

[1] FAC CIENCIAS,DEPT BIOQUIM BIOL MOL & QUIM ORGAN,E-29071 MALAGA,SPAIN

来源：

THEORETICA CHIMICA ACTA | 1996年 / 94卷 / 01期

关键词：

AM1; Wolff Rearrangement; beta-Oxy-alpha-Diazo carbonyl compounds;

D O I：

10.1007/BF00190152

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The study of several thermal processes involved in the beta-oxy-alpha-diazo carbonyl compounds chemistry at the AM1 semiempirical level is reported. Principally, our study focussed on competitive Wolff and 1,2-hydride rearrangement reactions involving nitrogen elimination that a particular type of beta-oxy-alpha-diazo carbonyl compounds (see scheme 1) can undergo under certain conditions. The AM1 results provide a reasonable description of the energy-related and structural aspects involved in the elementary processes considered.

引用

页码：13 / 22

页数：10

共 38 条

[1] OXIRENES AND KETOCARBENES FROM ALPHA-DIAZOKETONE PHOTOLYSIS - EXPERIMENTS IN RARE-GAS MATRICES - RELATIVE STABILITIES AND ISOMERIZATION BARRIERS FROM MNDOC-BWEN CALCULATIONS [J].

BACHMANN, C ;

NGUESSAN, TY ;

DEBU, F ;

MONNIER, M ;

POURCIN, J ;

AYCARD, JP ;

BODOT, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (21) :7488-7497

[2] ON THE EXISTENCE OF STABLE STRUCTURAL ISOMERS OF KETENE - A THEORETICAL-STUDY OF THE C2H2O POTENTIAL-ENERGY SURFACE [J].

BOUMA, WJ ;

NOBES, RH ;

RADOM, L ;

WOODWARD, CE .

JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (10) :1869-1875

[3] MECHANISM OF WOLFF REARRANGEMENT [J].

CSIZMADIA, IG ;

FONT, J ;

STRAUSZ, OP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1968, 90 (26) :7360-+

[4] 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

[5]

FRATER G, 1970, J AM CHEM SOC, V92, P6654

[6]

HAYES RA, 1985, J AM CHEM SOC, V107, P7597

[7]

HERRERA FJL, 1994, TETRAHEDRON LETT, V35, P2929

[8]

HERRERA FJL, 1993, TETRAHEDRON LETT, V34, P3467

[9] MECHANISM OF WOLFF REARRANGEMENT OF ALPHA-DIAZOHOMOADAMANTANONE - EVIDENCE AGAINST OXIREN PARTICIPATION [J].

MAJERSKI, Z ;

REDVANLY, CS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1972, (11) :694-&

[10] DECOMPOSITION OF ALPHA-DIAZO-KETONES - OXIREN-OXOCARBENE EQUILIBRIUM [J].

MATLIN, SA ;

SAMMES, PG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1972, (20) :2623-&

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