Solvent perturbs the reactivity of tert-butylcarbene

被引：29

作者：

Ruck, RT ^{[1
]}

Jones, M ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 16期

关键词：

D O I：

10.1016/S0040-4039(98)00291-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two different sources of tert-butylcarbene are used to generate this reactive intermediate in a variety of solvents. Two products, 1,1-dimethylcyclopropane and 2-methyl-2-butene are formed. Solvents able to form an ylid or complex with the carbene strongly favor the alkene product. (C) 1998 Elsevier Science Ltd. All rights reserved.

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页码：2277 / 2280

页数：4

相关论文

共 13 条

[1] YLIDE FORMATION AND REARRANGEMENT IN REACTION OF CARBENE WITH DIVALENT SULFUR-COMPOUNDS [J].

ANDO, W .

ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (05) :179-185

[2] A COMPUTATIONAL AND EXPERIMENTAL INVESTIGATION OF FREE TERT-BUTYLMETHYLENE, A CARBENE STABILIZED BY SIGMA-BOND PARTICIPATION [J].

ARMSTRONG, BM ;

MCKEE, ML ;

SHEVLIN, PB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) :3685-3689

[3] ROLES OF MULTIPLICITY AND ELECTRONIC EXCITATION ON INTRA-MOLECULAR REACTIONS OF ALKYLCARBENES IN CONDENSED PHASE [J].

CHANG, KT ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) :5082-5084

[4] Stereodirecting effects in the characterization of ylide intermediates in reactions of singlet methylene with an allylic ether and an allylic chloride [J].

Cubbage, JW ;

Edelbach, BL ;

Kuen, KS ;

DeLuca, JP .

TETRAHEDRON, 1997, 53 (29) :9823-9834

[5] UNTERSUCHUNGEN UBER CARBENE .9. CARBENE AUS SULFONIUMSALZEN [J].

FRANZEN, V ;

SCHMIDT, HJ ;

MERTZ, C .

CHEMISCHE BERICHTE-RECUEIL, 1961, 94 (11) :2942-2950

[6] CARBENOID AND CATIONOID DECOMPOSITION OF DIAZO HYDROCARBONS DERIVED FROM TOSYLHYDRAZONES [J].

FRIEDMAN, L ;

SHECHTER, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5512-5513

[7] A PHOTOCHEMICAL SOURCE OF REAL ALKYLCARBENES [J].

GLICK, HC ;

LIKHOTVORIK, IR ;

JONES, M .

TETRAHEDRON LETTERS, 1995, 36 (32) :5715-5718

[8] Ab initio study of the stability of the ylide-like intermediate methyleneoxonium in the reaction between singlet methylene and water [J].

Gonzalez, C ;

RestrepoCossio, A ;

Marquez, M ;

Wiberg, KB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (23) :5408-5411

[9]

Jackson J.E., 1994, ADV CARBENE CHEM, V1, P89

[10]

KIRMSE W, 1971, CARBENE CHEM, P422