ELECTRONIC EFFECTS IN PI-FACIALLY STEREOSELECTIVE EPOXIDATION OF PHENYLTRIFLUOROMETHYLPROPENOL

被引：10

作者：

CASHER, O ^{[1
]}

OHAGAN, D ^{[1
]}

ROSENKRANZ, CA ^{[1
]}

RZEPA, HS ^{[1
]}

ZAIDI, NA ^{[1
]}

机构：

[1] UNIV DURHAM,DEPT CHEM,DURHAM DM1 3LE,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1993年 / 17期

关键词：

D O I：

10.1039/c39930001337

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

AM1, PM3 and ab initio 6-31G* calculations indicate that stereoselective epoxidation of the alkene 3 arises from stereoelectronic control exerted via a CF3-C bond orientated anti to the alkene plane for steric reasons, in contrast to a previously proposed model for epoxidation of allylic fluorides in which the F-C and alkene bonds are oriented syn.

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页码：1337 / 1340

页数：4

相关论文

共 26 条

[1]

ANAH NT, 1977, NOUV J CHIM, V1, P61

[2] TRANSITION STRUCTURE FOR THE EPOXIDATION OF ALKENES WITH PEROXY ACIDS - A THEORETICAL-STUDY [J].

BACH, RD ;

OWENSBY, AL ;

GONZALEZ, C ;

SCHLEGEL, HB ;

MCDOUALL, JJW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (06) :2338-2339

[3] MECHANISM OF OXYGEN ATOM TRANSFER FROM OXAZIRIDINE TO A LITHIUM ENOLATE - A THEORETICAL-STUDY [J].

BACH, RD ;

ANDRES, JL ;

DAVIS, FA .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :613-618

[4]

BROUGHTON HB, 1992, J CHEM SOC CHEM COMM, P988

[5] ARYL GROUP PI-FACIAL ELECTROSTATIC ASYMMETRY AS A CONTRIBUTING FACTOR TO CHIRAL RESOLUTION ON BETA-CYCLODEXTRIN HPLC PHASES [J].

CAMILLERI, P ;

EDWARDS, AJ ;

RZEPA, HS ;

GREEN, SM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (16) :1122-1124

[6] REVERSAL OF PI-FACIAL DIASTEREOSELECTION UPON ELECTRONEGATIVE SUBSTITUTION OF THE SUBSTRATE AND THE REAGENT [J].

CIEPLAK, AS ;

TAIT, BD ;

JOHNSON, CR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (22) :8447-8462

[7]

FRISCH MJ, 1992, GAUSSIAN92

[8] ELECTRONIC EFFECTS ON PI-FACIAL STEREOSELECTIVITY IN ELECTROPHILIC ADDITIONS TO ALLYLIC BONDS - STEREOSELECTIVE EPOXIDATION OF ALLYLIC FLUORIDES [J].

FUJITA, M ;

ISHIZUKA, H ;

OGURA, K .

TETRAHEDRON LETTERS, 1991, 32 (44) :6355-6358

[9] A MOLECULAR-ORBITAL AND CRYSTALLOGRAPHIC STUDY OF THE STRUCTURE AND PI-FACIAL REGIOSELECTIVITY OF 9-CHLORO-1,4,5,8-TETRAHYDRO-4A,8A-METHANONAPHTHALENE [J].

HALTON, B ;

BOESE, R ;

RZEPA, HS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :447-&

[10]

HOLDER AJ, KS66216