CARBOETHOXYCARBENE - A LASER FLASH-PHOTOLYSIS STUDY

被引:47
作者
TOSCANO, JP
PLATZ, MS
NIKOLAEV, V
POPIC, V
机构
[1] OHIO STATE UNIV,DEPT CHEM,COLUMBUS,OH 43210
[2] ST PETERSBURG STATE UNIV,ST PETERSBURG,RUSSIA
关键词
D O I
10.1021/ja00097a023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Laser flash photolysis of ethyldiazoacetate (351 nm, 17 ns) generates carboethoxycarbene, which can be intercepted with either pyridine or acetone to produce a UV-vis active ylide. Analysis of the yield of ylide as a function of either pyridine or acetone concentration leads to estimates of the carbene lifetime. Absolute rate constants of reaction of carboethoxycarbene with alcohols, sulfides, ethers, and alkenes were deduced.
引用
收藏
页码:8146 / 8151
页数:6
相关论文
共 88 条
[21]  
FIESER LF, 1967, REAGENTS ORGANIC SYN, V1, P367
[22]  
FOX JM, 1992, TETRAHEDRON LETT, V33, P502
[23]   LASER FLASH-PHOTOLYSIS STUDIES OF METHOXYCARBONYL PHENYL CARBENE AND ITS DERIVED CARBONYL OXIDE AT ROOM-TEMPERATURE [J].
FUJIWARA, Y ;
TANIMOTO, Y ;
ITOH, M ;
HIRAI, K ;
TOMIOKA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :1942-1946
[24]  
HALL GE, 1965, TETRAHEDRON LETT, P437
[25]   PHOTOCHEMICAL WOLFF REARRANGEMENT OF A TRIPLET GROUND-STATE CARBENE [J].
HAYES, RA ;
HESS, TC ;
MCMAHON, RJ ;
CHAPMAN, OL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (26) :7786-7787
[26]  
HELGEN LE, 1965, THESIS YALE U NEW HA
[27]   ELECTRON-PARAMAGNETIC RESONANCE-SPECTRA OF CARBALKOXYCARBENES - GEOMETRIC ISOMERISM IN GROUND-STATE TRIPLETS [J].
HUTTON, RS ;
ROTH, HD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (13) :4324-4325
[28]   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
[29]   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
[30]  
JACKSON JE, 1989, TETRAHEDRON LETT, V30, P1355