Reaction of benzyl Grignard reagents with trifluoroacetyldihydropyrans and other cyclic β-alkoxy-α,β-unsaturated trifluoromethylketones

被引:20
作者
Coles, SJ
Mellor, JM [1 ]
El-Sagheer, AH
Salem, EEDM
Metwally, RN
机构
[1] Univ Southampton, Dept Chem, Southampton SO17 1BJ, Hants, England
[2] Suez Canal Univ, Fac Sci, Dept Chem, Ismailia, Egypt
[3] Suez Canal Univ, Fac Petr & Min Engn, Dept Sci & Maths, Suez, Egypt
关键词
additions; Grignard reagents; trifluoromethylketones;
D O I
10.1016/S0040-4020(00)00976-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Benzyl Grignard reagents react with cyclic beta -alkoxy-alpha,beta -unsaturated trifluoromethyl ketones by 1,2-addition to afford unsaturated allylic alcohols in high yield. The factors determining the balance between 1,2- and 1,4-addition to unsaturated ketones are discussed. The structures of major and minor products are established by single crystal X-ray diffraction studies. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10057 / 10066
页数:10
相关论文
共 40 条
[1]   Synthesis of αβ-unsaturated trifluoromethyl ketones from 4-dimethylamino-1,1,1-trifluorobut-3-ene-2-one by addition of Grignard reagents [J].
Andrew, RJ ;
Mellor, JM .
TETRAHEDRON, 2000, 56 (37) :7261-7266
[2]  
ARMSTRONG A, 1995, COMPREHENSIVE ORGANI, V1, P293
[3]   MECHANISM OF THE REACTION BETWEEN BENZYLMAGNESIUM CHLORIDE AND CARBONYL-COMPOUNDS - A DETAILED STUDY WITH FORMALDEHYDE [J].
BENKESER, RA ;
SNYDER, DC .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (07) :1243-1249
[4]   NEW APPROACH TO THE MECHANISM OF THE REACTION BETWEEN BENZYL GRIGNARD-REAGENTS AND CARBONYL-COMPOUNDS [J].
BERNARDON, C ;
DEBERLY, A .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (03) :463-468
[5]   Outlier treatment in data merging [J].
Blessing, RH .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1997, 30 :421-426
[6]   Unexpected regioselectivity in the attack of vinyl Grignard reagents to bis(2-benzothiazolyl)ketone [J].
Boga, C ;
Forlani, L ;
Todesco, PE .
TETRAHEDRON LETTERS, 1997, 38 (27) :4845-4848
[7]   LOW-TEMPERATURES FAVOR KINETIC 1,4-ADDITION OVER 1,2-ADDITION OF ORGANOLITHIUMS TO ALPHA-ENONES - THE CRUCIAL ROLE OF ION-PAIRING [J].
COHEN, T ;
ABRAHAM, WD ;
MYERS, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (25) :7923-7924
[8]   FACTORS CONTROLLING REGIOSELECTIVITY OF ADDITIONS TO ALPHA-ENONES .3. REACTIONS OF 3-ARYL ALPHA-ENONES WITH PHOSPHORYLATED ANIONS [J].
COSSENTINI, M ;
DESCHAMPS, B ;
ANH, NT ;
SEYDENPENNE, J .
TETRAHEDRON, 1977, 33 (04) :409-412
[9]   ORTHO CONJUGATE ADDITION OF BENZYL GRIGNARDS - A REMARKABLE COPPER EFFECT [J].
DANISHEFSKY, S ;
MIGDALOF, BH .
JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (19) :1107-+
[10]   STEREOCHEMISTRY OF ADDITION OF ALLYL GRIGNARD-REAGENTS TO (R)-(+)-PULEGONE AND OTHER ALPHA,BETA-ETHYLENIC KETONES [J].
ELIDRISSI, M ;
SANTELLI, M .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1010-1016