PHOTOLYSIS OF ALKYLHALODIAZIRINES - 2 PATHWAYS FOR VINYL HALIDE FORMATION

被引:44
作者
LAVILLA, JA [1 ]
GOODMAN, JL [1 ]
机构
[1] UNIV ROCHESTER,DEPT CHEM,ROCHESTER,NY 14627
基金
美国国家科学基金会;
关键词
D O I
10.1016/S0040-4039(00)97817-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Photoacoustic calorimetry and product studios on the photochemical decomposition of methylhalodiazirines indicate two pathways for the formation of vinyl halides: 1) a [1,2] intramolecular hydrogen shift of the initially formed methylhalocarbene, 2) an excited state pathway which circumvents the ground state carbene. Results suggest that carbene/olefin or carbene/alcohol complexes are not involved in vinyl halide formation. © 1990.
引用
收藏
页码:5109 / 5112
页数:4
相关论文
共 26 条
[1]   ELEMENTARY PROCESSES IN THE GAS-PHASE PHOTODECOMPOSITION OF SINGLET AND TRIPLET 3-CHLORO-3-METHYLDIAZIRINE [J].
AVILA, MJ ;
BECERRA, R ;
FIGUERA, JM ;
RODRIGUEZ, JC ;
TOBAR, A ;
MARTINEZUTRILLA, R .
JOURNAL OF PHYSICAL CHEMISTRY, 1985, 89 (25) :5489-5495
[2]  
BECERRA R, 1981, AN QUIM A-FIS TEC, V77, P63
[3]   THE DEVELOPMENT AND USE OF QUANTUM-MECHANICAL MOLECULAR-MODELS .76. AM1 - A NEW GENERAL-PURPOSE QUANTUM-MECHANICAL MOLECULAR-MODEL [J].
DEWAR, MJS ;
ZOEBISCH, EG ;
HEALY, EF ;
STEWART, JJP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (13) :3902-3909
[4]   REACTIONS OF DIMETHOXYCARBENE AND FLUOROMETHOXYCARBENE WITH HYDROXYL COMPOUNDS - ABSOLUTE RATE CONSTANTS AND THE HEAT OF FORMATION OF DIMETHOXYCARBENE [J].
DU, XM ;
FAN, H ;
GOODMAN, JL ;
KESSELMAYER, MA ;
KROGHJESPERSEN, K ;
LAVILLA, JA ;
MOSS, RA ;
SHEN, S ;
SHERIDAN, RS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1920-1926
[5]   PHOTOLYSIS OF 3-METHYL-3-CHLORODIAZIRINE [J].
FREY, HM ;
PENNY, DE .
JOURNAL OF THE CHEMICAL SOCIETY-FARADAY TRANSACTIONS I, 1977, 73 :2010-2024
[7]   STUDY OF 124-KILODALTON OAT PHYTOCHROME PHOTOCONVERSIONS INVITRO WITH LASER-INDUCED OPTOACOUSTIC SPECTROSCOPY [J].
HEIHOFF, K ;
BRASLAVSKY, SE ;
SCHAFFNER, K .
BIOCHEMISTRY, 1987, 26 (05) :1422-1427
[8]   THE EXPERIMENTAL HEATS OF FORMATION AND KINETICS OF 1,3-BIRADICALS USING TIME-RESOLVED PHOTOACOUSTIC CALORIMETRY [J].
HERMAN, MS ;
GOODMAN, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2681-2683
[9]   DETERMINATION OF THE ENTHALPY AND REACTION VOLUME CHANGES OF ORGANIC PHOTOREACTIONS USING PHOTOACOUSTIC CALORIMETRY [J].
HERMAN, MS ;
GOODMAN, JL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (05) :1849-1854
[10]   KINETICS OF A CARBENE REARRANGEMENT - THE 1,2-CARBON MIGRATION OF CYCLOPROPYLCHLOROCARBENE [J].
HO, GJ ;
KROGHJESPERSEN, K ;
MOSS, RA ;
SHEN, S ;
SHERIDAN, RS ;
SUBRAMANIAN, R .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) :6875-6877