X-RAY-DIFFRACTION STUDIES OF CRYSTALLINE TRIHALOMETHYL KETONES (RCOCX3) REVEAL AN UNUSUAL STRUCTURAL DEFORMATION ABOUT THE CARBONYL GROUP

被引：27
作者：
COREY, EJ
LINK, JO
SARSHAR, S
SHAO, Y
机构：
[1] Deparment of Chemistry, Harvard University, Cambridge
来源：
TETRAHEDRON LETTERS | 1992年 / 33卷 / 47期
关键词：
D O I：
10.1016/S0040-4039(00)60847-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
X-ray crystallographic studies of a set of trihalomethyl ketones (4, 5, and 6) indicate that the carbonyl oxygen is displaced significantly toward the trihalomethyl group, probably as a consequence of oxygen lone pair delocalization into the sigma* orbital of CO-CX3.
引用
收藏
页码：7103 / 7106
页数：4
相关论文
共 14 条
[1]  
BURGE HB, 1985, HELV CHIM ACTA, V68, P76
[2]   1-MESITYL-2,2,2-TRIFLUOROETHANOL, AN OUTSTANDING NEW CHIRAL CONTROLLER FOR CATALYZED DIELS-ALDER REACTIONS [J].
COREY, EJ ;
CHENG, XM ;
CIMPRICH, KA .
TETRAHEDRON LETTERS, 1991, 32 (47) :6839-6842
[3]   AN EFFICIENT AND CATALYTICALLY ENANTIOSELECTIVE ROUTE TO (S)-(-)-PHENYLOXIRANE [J].
COREY, EJ ;
SHIBATA, S ;
BAKSHI, RK .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (12) :2861-2863
[4]   A NEW CHIRAL CATALYST FOR THE ENANTIOSELECTIVE SYNTHESIS OF SECONDARY ALCOHOLS AND DEUTERATED PRIMARY ALCOHOLS BY CARBONYL REDUCTION [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1989, 30 (46) :6275-6278
[5]   A GENERAL, CATALYTIC, AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].
COREY, EJ ;
LINK, JO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (05) :1906-1908
[6]   2 EFFECTIVE PROCEDURES FOR THE SYNTHESIS OF TRICHLOROMETHYL KETONES, USEFUL PRECURSORS OF CHIRAL ALPHA-AMINO AND ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
LINK, JO ;
SHAO, Y .
TETRAHEDRON LETTERS, 1992, 33 (24) :3435-3438
[7]   A NEW SYSTEM FOR CATALYTIC ENANTIOSELECTIVE REDUCTION OF ACHIRAL KETONES TO CHIRAL ALCOHOLS - SYNTHESIS OF CHIRAL ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
BAKSHI, RK .
TETRAHEDRON LETTERS, 1990, 31 (05) :611-614
[8]   REMARKABLY EFFECTIVE AND SIMPLE SYNTHESES OF ENANTIOMERICALLY PURE SECONDARY CARBINOLS FROM ACHIRAL KETONES [J].
COREY, EJ ;
CHENG, XM ;
CIMPRICH, KA ;
SARSHAR, S .
TETRAHEDRON LETTERS, 1991, 32 (47) :6835-6838
[9]   A NEW PROCESS FOR THE ENANTIOSELECTIVE SYNTHESIS OF CHIRAL ALPHA-ARYLOXY AND ALPHA-HYDROXY ACIDS [J].
COREY, EJ ;
LINK, JO .
TETRAHEDRON LETTERS, 1992, 33 (24) :3431-3434
[10]   HIGHLY ENANTIOSELECTIVE BORANE REDUCTION OF KETONES CATALYZED BY CHIRAL OXAZABOROLIDINES - MECHANISM AND SYNTHETIC IMPLICATIONS [J].
COREY, EJ ;
BAKSHI, RK ;
SHIBATA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (18) :5551-5553
12