AN EXTRAORDINARY ISOTOPE EFFECT IN A CARBENE REARRANGEMENT

被引:20
作者
MOSS, RA
HO, GJ
LIU, WG
SIERAKOWSKI, C
机构
[1] Department of Chemistry, Rutgers University, New Brunswick
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)74240-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The kinetic isotope effect for the 1,2 approximately H/1,2 approximately D shift in neopentylfluorocarbenes 2a-2c is about 5.
引用
收藏
页码:4287 / 4290
页数:4
相关论文
共 16 条
[1]   PYRIDINE YLIDE FORMATION BY CAPTURE OF PHENYLCHLOROCARBENE AND TERT-BUTYLCHLOROCARBENE - REACTION-RATES OF AN ALKYLCHLOROCARBENE BY LASER FLASH-PHOTOLYSIS [J].
JACKSON, JE ;
SOUNDARARAJAN, N ;
PLATZ, MS ;
LIU, MTH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (16) :5595-5596
[2]   MEASUREMENT OF THE ABSOLUTE RATE OF 1,2-HYDROGEN MIGRATION IN BENZYLCHLOROCARBENE [J].
JACKSON, JE ;
SOUNDARARAJAN, N ;
WHITE, W ;
LIU, MTH ;
BONNEAU, R ;
PLATZ, MS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6874-6875
[3]   OBSERVATIONS ON THE GEOMETRY OF HYDROGEN TRANSFER IN [1,5]SIGMATROPIC REARRANGEMENTS [J].
KWART, H ;
BRECHBIEL, MW ;
ACHESON, RM ;
WARD, DC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (17) :4671-4672
[4]   THE 1,2-HYDROGEN-SHIFT REARRANGEMENT IN ALKYLCHLOROCARBENES [J].
LAVILLA, JA ;
GOODMAN, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6877-6878
[5]   PHOTOLYSIS OF ALKYLHALODIAZIRINES - 2 PATHWAYS FOR VINYL HALIDE FORMATION [J].
LAVILLA, JA ;
GOODMAN, JL .
TETRAHEDRON LETTERS, 1990, 31 (36) :5109-5112
[6]   BENZYLCHLOROCARBENE - KINETICS PARAMETERS FOR 1,2-H MIGRATION, UV ABSORPTION-SPECTRUM, AND MECHANISM FOR ADDITION TO ALKENES [J].
LIU, MTH ;
BONNEAU, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (10) :3915-3919
[7]   THERMOLYSIS AND PHOTOLYSIS OF 3-CHLORO-3-BENZYLDIAZIRINES IN ALKENES - EVIDENCE FOR A CARBENE ALKENE COMPLEX [J].
LIU, MTH ;
SOUNDARARAJAN, N ;
PAIKE, N ;
SUBRAMANIAN, R .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (19) :4223-4227
[8]  
MODARELLI DA, UNPUB J AM CHEM SOC
[9]   KINETICS OF A 1,3-CH CARBENE INSERTION REACTION - TERT-BUTYLCHLOROCARBENE [J].
MOSS, RA ;
HO, GJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (14) :5642-5644
[10]   KINETICS OF ALKYLHALOCARBENE REARRANGEMENTS - MODULATION BY FLUORINE SUBSTITUENTS [J].
MOSS, RA ;
HO, GJ ;
LIU, WG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :959-963