THE REACTION OF DIMETHYLDIOXIRANE WITH ALKYNES

被引:35
作者
MURRAY, RW
SINGH, M
机构
[1] Department of Chemistry, University of Missouri-St. Louis, St. Louis
关键词
D O I
10.1021/jo00071a016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of dimethyldioxirane with several alkynes gives products which are conveniently rationalized by postulating the intermediacy of oxirenes and oxocarbenes. The latter serve as precursors to H atom or methyl group migration products, as well as to cyclopropane insertion products in some cases. Alkenes, derived from some of these carbene reactions, are partially converted to epoxides.
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收藏
页码:5076 / 5080
页数:5
相关论文
共 30 条
[1]   SPECTRAL AND CHEMICAL-PROPERTIES OF DIMETHYLDIOXIRANE AS DETERMINED BY EXPERIMENT AND ABINITIO CALCULATIONS [J].
ADAM, W ;
CHAN, YY ;
CREMER, D ;
GAUSS, J ;
SCHEUTZOW, D ;
SCHINDLER, M .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (13) :2800-2803
[2]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[3]  
ADAM W, 1992, ORGANIC PEROXIDES, pCH4
[4]   PREPARATION AND SPECTROSCOPIC PROPERTIES OF 2,2,4,5-TETRAMETHYLHEX-4-EN-3-ONE [J].
ALJALLO, HNA ;
ARNOLD, BJ ;
ROTHWELL, BJ ;
WAIGHT, ES .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (05) :846-&
[5]   EPOXIDATION OF ALKENES BY DIMETHYLDIOXIRANE - EVIDENCE FOR A SPIRO TRANSITION-STATE [J].
BAUMSTARK, AL ;
MCCLOSKEY, CJ .
TETRAHEDRON LETTERS, 1987, 28 (29) :3311-3314
[6]   STRUCTURAL EFFECTS IN SOLVOLYTIC REACTIONS .17. SOLVOLYSIS OF 1-ARYL-1-CYCLOPROPYL-1-ETHYL P-NITROBENZOATES - EVIDENCE FOR MAJOR INCREASES IN ELECTRON SUPPLY BY CYCLOPROPYL GROUP WITH INCREASING ELECTRON DEMAND AT CATIONIC CENTER - EFFECT OF SUBSTITUENTS ON CYCLOPROPANE RING - SIGMA CONJUGATION VS SIGMA PARTICIPATION [J].
BROWN, HC ;
PETERS, EN ;
RAVINDRANATHAN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (02) :505-509
[7]   PERACID OXIDATION OF ACETYLENES - 1,2-METHYL MIGRATION, CYCLOPROPANE FORMATION, AND STEREOSELECTIVE 1,5-TRANSANNULAR AND 1,6-TRANSANNULAR INSERTION [J].
CIABATTONI, J ;
CAMPBELL, RA ;
RENNER, CA ;
CONCANNON, PW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (12) :3826-+
[8]   BASE-PROMOTED REACTIONS OF EPOXIDES .3. CARBENOID DECOMPOSITION IN ACYCLIC DERIVATIVES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (17) :4526-&
[9]   PERACID OXIDATIONS OF CYCLOPROPENES AND CYCLOPROPENONES [J].
CRANDALL, JK ;
CONOVER, WW .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (07) :1323-1327
[10]   OXIDATION OF ALKYNES BY DIOXIRANES [J].
CURCI, R ;
FIORENTINO, M ;
FUSCO, C ;
MELLO, R ;
BALLISTRERI, FP ;
FAILLA, S ;
TOMASELLI, GA .
TETRAHEDRON LETTERS, 1992, 33 (51) :7929-7932