Oxidation of benzyl alcohols by dimethyldioxirane. The question of concerted versus stepwise mechanisms probed by kinetic isotope effects

被引:14
作者
Angelis, YS [1 ]
Hatzakis, NS [1 ]
Smonou, I [1 ]
Orfanopoulos, M [1 ]
机构
[1] Univ Crete, Dept Chem, Iraklion 71409, Crete, Greece
关键词
dioxiranes; isotope effects; mechanisms;
D O I
10.1016/S0040-4039(01)00539-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The primary and beta -secondary kinetic isotope effects in the oxidation of secondary alcohols with dimethyl dioxirane were measured. The substantial primary and the absence of a P-secondary kinetic isotope effect support a concerted mechanism for the title reaction. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3753 / 3756
页数:4
相关论文
共 20 条
[1]   Asymmetric C-H oxidation of vic-diols to α-hydroxy ketones by a fructose-derived dioxirane:: Electronic effects on the enantioselectivity of oxygen transfer [J].
Adam, W ;
Saha-Möller, CR ;
Zhao, CG .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (20) :7492-7497
[2]   OXIDATION OF ALLYLIC ALCOHOLS BY DIMETHYLDIOXIRANE - COMPETITION REACTION BETWEEN EPOXIDATION AND C-H INSERTION [J].
ADAM, W ;
PRECHTL, F ;
RICHTER, MJ ;
SMERZ, AK .
TETRAHEDRON LETTERS, 1993, 34 (52) :8427-8430
[3]   DIOXIRANES - A NEW CLASS OF POWERFUL OXIDANTS [J].
ADAM, W ;
CURCI, R ;
EDWARDS, JO .
ACCOUNTS OF CHEMICAL RESEARCH, 1989, 22 (06) :205-211
[4]   Secondary isotope effects in dioxirane epoxidations. Concerted or step-wise mechanism? [J].
Angelis, Y ;
Zhang, XJ ;
Orfanopoulos, M .
TETRAHEDRON LETTERS, 1996, 37 (33) :5991-5994
[5]   SELECTIVE OXIDATION OF DIOLS BY H2O2/TS-1 SYSTEM AND BY DMDO [J].
BOVICELLI, P ;
LUPATTELLI, P ;
SANETTI, A ;
MINCIONE, E .
TETRAHEDRON LETTERS, 1994, 35 (45) :8477-8480
[6]   EFFICIENT DESYMMETRIZATION OF 1,2-DIOL AND 1,3-DIOL BY DIMETHYLDIOXIRANE [J].
BOVICELLI, P ;
LUPATTELLI, P ;
SANETTI, A ;
MINCIONE, E .
TETRAHEDRON LETTERS, 1995, 36 (17) :3031-3034
[7]  
Carpenter B.K., 1984, DETERMINATION ORG
[8]   SELECTIVE OXIDATION OF TERTIARY-SECONDARY VIC-DIOLS TO ALPHA-HYDROXY KETONES BY DIOXIRANES [J].
CURCI, R ;
D'ACCOLTI, L ;
DETOMASO, A ;
FUSCO, C ;
TAKEUCHI, K ;
OHGA, Y ;
EATON, PE ;
YIP, YC .
TETRAHEDRON LETTERS, 1993, 34 (28) :4559-4562
[9]  
DACOLTI L, 1993, J ORG CHEM, V58, P3600
[10]  
Higgens R., 1968, ADV CHEM SER, V77, P102