CARBONYL OXIDE CHEMISTRY .2. SUBSTITUENT AND SOLVENT EFFECTS ON THE CHEMICAL BEHAVIOR OF CARBONYL-OXIDES

被引:14
作者
IESCE, MR [1 ]
CERMOLA, F [1 ]
GRAZIANO, ML [1 ]
SCARPATI, R [1 ]
机构
[1] UNIV NAPOLI FEDERICO II,DIPARTIMENTO CHIM ORGAN & BIOL,I-80134 NAPLES,ITALY
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 01期
关键词
D O I
10.1039/p19940000147
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Comparison of the behaviour in polar and apolar solvents at various concentrations of the monoaryl carbonyl oxides 1 bearing an electron-withdrawing or an electron-donating group, respectively, on the aryl substituent is reported. The results are consistent with the conversion pathways reported in Scheme 1 and show that the electron-donating group increases the intramolecular oxygen-transfer potential of the system. It is also proposed that under some experimental conditions the carbonyl oxides so substituted mainly isomerize into dioxiranes 11.
引用
收藏
页码:147 / 152
页数:6
相关论文
共 33 条
[11]   THEORETICAL DETERMINATION OF MOLECULAR-STRUCTURE AND CONFORMATION .18. ON THE FORMATION OF EPOXIDES DURING THE OZONOLYSIS OF ALKENES [J].
CREMER, D ;
BOCK, CW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (12) :3375-3379
[12]   FORMATION OF DIOXIRANE FROM CARBONYL OXIDE [J].
CREMER, D ;
SCHMIDT, T ;
GAUSS, J ;
RADHAKRISHNAN, TP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (03) :427-428
[13]   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
[14]  
CURCI R, 1990, ADV OXYGENATED PROCE, V2, P1
[15]  
DENNY RW, 1973, ORG REACTIONS, V20, P185
[16]   MECHANISM OF OXYGEN ACTIVATION BY PTERIDINE-DEPENDENT MONOOXYGENASES [J].
DIX, TA ;
BENKOVIC, SJ .
ACCOUNTS OF CHEMICAL RESEARCH, 1988, 21 (03) :101-107
[17]   OPTICAL MODULATION SPECTROSCOPY - A STUDY OF THE SELF-REACTION OF BENZOPHENONE OXIDE [J].
GIRARD, M ;
GRILLER, D .
JOURNAL OF PHYSICAL CHEMISTRY, 1986, 90 (26) :6801-6804
[18]   1,3-DIPOLAR CYCLOADDITION REACTIONS .53. QUESTION OF 1,3-DIPOLAR NATURE OF DELTA2-OXAZOLIN-5-ONES [J].
GOTTHARDT, H ;
HUISGEN, R ;
BAYER, HO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (14) :4340-+
[19]   REGIO-SELECTIVITY AND STEREO-SELECTIVITY OF THE 1ST [3 + 2] CYCLO-ADDITION OF CARBONYL OXIDE TO ELECTRON-POOR ALKENES - BIDIRECTIONALITY OF THE 1,3-DIPOLE [J].
GRAZIANO, ML ;
IESCE, MR ;
CERMOLA, F ;
GIORDANO, F ;
SCARPARTI, R .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) :1608-1610
[20]   PHOTOSENSITIZED OXIDATION OF FURANS .13. TRAPPING REACTIONS OF THE CARBONYL OXIDES OBTAINED FROM SOME 2-METHOXY-5-PHENYLFURANS [J].
GRAZIANO, ML ;
IESCE, MR ;
CIMMINIELLO, G ;
SCARPATI, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (07) :1699-1704