Dioxirane epoxidations of 1,1-disubstituted ethylenes. Probing for radical pathways by computations and experiments

被引:26
作者
Liu, J
Houk, KN [1 ]
Dinoi, A
Fusco, C
Curci, R
机构
[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA
[2] Univ Bari, Dept Chem, Ctr MISO, CNR, I-70126 Bari, Italy
关键词
D O I
10.1021/jo981050d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:8565 / 8569
页数:5
相关论文
共 34 条
[1]   THERMALLY AND PHOTOCHEMICALLY INITIATED RADICAL CHAIN DECOMPOSITION OF KETONE-FREE METHYL(TRIFLUOROMETHYL)DIOXIRANE [J].
ADAM, W ;
CURCI, R ;
NUNEZ, MEG ;
MELLO, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (20) :7654-7658
[2]   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
[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]  
ADAM W, 1993, TOP CURR CHEM, V164, P45
[5]   Epoxidation and oxygen insertion into alkane CH bonds by dioxirane do not involve detectable radical pathways [J].
Adam, W ;
Curci, R ;
D'Accolti, L ;
Dinoi, A ;
Fusco, C ;
Gasparrini, F ;
Kluge, R ;
Paredes, R ;
Schulz, M ;
Smerz, AK ;
Veloza, LA ;
Weinkotz, S ;
Winde, R .
CHEMISTRY-A EUROPEAN JOURNAL, 1997, 3 (01) :105-109
[6]   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
[7]  
[Anonymous], ORGANIC PEROXIDES
[8]   ELECTRONIC-STRUCTURE AND REACTIVITY OF DIOXIRANE AND CARBONYL OXIDE [J].
BACH, RD ;
ANDRES, JL ;
OWENSBY, AL ;
SCHLEGEL, HB ;
MCDOUALL, JJW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7207-7217
[9]   Nature of the transition structure for alkene epoxidation by peroxyformic acid, dioxirane, and dimethyldioxirane: A comparison of B3LYP density functional theory with higher computational levels [J].
Bach, RD ;
Glukhovtsev, MN ;
Gonzalez, C ;
Marquez, M ;
Estevez, CM ;
Baboul, AG ;
Schlegel, HB .
JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (34) :6092-6100
[10]   EPOXIDATION BY DIMETHYLDIOXIRANE - ELECTRONIC AND STERIC EFFECTS [J].
BAUMSTARK, AL ;
VASQUEZ, PC .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (15) :3437-3439