A NEW MECHANISM FOR THE PHOTOCLEAVAGE OF MONOTHIOIMIDES

被引:5
作者
FU, TY [1 ]
SCHEFFER, JR [1 ]
TROTTER, J [1 ]
机构
[1] UNIV BRITISH COLUMBIA,DEPT CHEM,VANCOUVER V6T 1Z1,BC,CANADA
基金
加拿大自然科学与工程研究理事会;
关键词
D O I
10.1016/S0040-4039(00)76873-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Based on solid state structure-reactivity correlation studies and on deuterium labeling experiments, it is concluded that the photochemical formation of thiobenzanilides 2a-d from monothioimides 1a-d does not involve initial gamma-hydrogen atom abstraction as originally suggested in the literature. Alternative mechanistic possibilities are presented and discussed.
引用
收藏
页码:3235 / 3238
页数:4
相关论文
共 8 条
[1]   PHOTOCHEMICAL TRANSFORMATIONS .33. PHOTOLYSIS OF THIOBENZOIC ACID O-ESTERS .4. PHOTOLYSIS OF O-PHENETHYL THIOBENZOATE DERIVATIVES AND FORMATION OF THIOKETONES [J].
BARTON, DHR ;
BOLTON, M ;
MAGNUS, PD ;
WEST, PJ .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (15) :1580-1583
[2]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[3]   CRYSTALLOGRAPHIC DETERMINATION OF THE PREFERRED GEOMETRY FOR INTRAMOLECULAR HYDROGEN-ATOM ABSTRACTION IN 1,8-CYCLOHEXADECANEDIONE [J].
LEWIS, TJ ;
RETTIG, SJ ;
SCHEFFER, JR ;
TROTTER, J .
MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 1992, 219 :17-28
[4]   COMPETITIVE TYPE-II ELIMINATIONS IN ALIPHATIC IMIDES [J].
MAZZOCCHI, PH ;
JAMESON, W ;
NISHIYAMA, T ;
DECAMP, A .
TETRAHEDRON LETTERS, 1980, 21 (11) :989-992
[5]   STEREOCHEMISTRY IN TRIVALENT NITROGEN-COMPOUNDS .28. CONFORMATIONAL-ANALYSIS AND TORSIONAL BARRIERS OF IMIDES AND TRIAMIDES [J].
NOE, EA ;
RABAN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (20) :5811-5820
[6]   PHOTOCHEMICAL DELTA-HYDROGEN ABSTRACTION FROM ACYCLIC AND SEMICYCLIC MONOTHIOIMIDES [J].
SAKAMOTO, M ;
TOHNISHI, M ;
FUJITA, T ;
WATANABE, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02) :347-351
[7]  
Scheffer J.R., 1987, ORGANIC SOLID STATE, P1
[8]  
Venkatesan K., 1991, PHOTOCHEMISTRY ORG C, P133