Sulfur ylides generated from the reaction of adamantylidene and phenylcarbene with sulfur substrates

被引:8
作者
Romashin, YN
Liu, MTH [1 ]
Hill, BT
Platz, MS
机构
[1] Univ Prince Edward Isl, Dept Chem, Charlottetown, PE C1A 4P3, Canada
[2] Ohio State Univ, Dept Chem, Columbus, OH 43210 USA
基金
美国国家科学基金会; 加拿大自然科学与工程研究理事会;
关键词
diazirine; carbene; adamantylidene; sulfur ylide; trimethylenesulfide; kinetics; laser flash photolysis;
D O I
10.1016/S0040-4039(03)01589-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of adamantylidene and phenylcarbene with ethylthiol, ethylene dithiol, allylethylsulfide, allylphenylsulfide, and trimethylenesulfide involves the formation of a sulfur ylide intermediate, followed by H-migration, 2,3-sigmatropic shift, or ring opening to give sulfides. The sulfur ylide formed in the reaction of phenylcarbene with trimethylenesulfide is directly observed by laser flash photolytic techniques. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6519 / 6521
页数:3
相关论文
共 13 条
[1]   Laser flash photolysis study of phenylcarbene and pentafluorophenylcarbene [J].
Admasu, A ;
Gudmundsdottir, AD ;
Platz, MS .
JOURNAL OF PHYSICAL CHEMISTRY A, 1997, 101 (20) :3832-3840
[2]  
Admasu A, 1997, J PHYS ORG CHEM, V10, P207, DOI 10.1002/(SICI)1099-1395(199704)10:4<207::AID-POC883>3.0.CO
[3]  
2-8
[4]   YLIDE FORMATION AND REARRANGEMENT IN REACTION OF CARBENE WITH DIVALENT SULFUR-COMPOUNDS [J].
ANDO, W .
ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (05) :179-185
[5]  
ANDO W, 1978, CHEM DIAZONIUM DIA 1, pCH9
[6]   Recent advances in asymmetric catalytic metal carbene transformations [J].
Doyle, MP ;
Forbes, DC .
CHEMICAL REVIEWS, 1998, 98 (02) :911-935
[7]   CATALYTIC METHODS FOR METAL CARBENE TRANSFORMATIONS [J].
DOYLE, MP .
CHEMICAL REVIEWS, 1986, 86 (05) :919-939
[8]  
ISAEV SD, 1973, ZH ORG KHIM+, V9, P724
[9]   YLIDE FORMATION FROM THE REACTION OF CARBENES AND CARBENOIDS WITH HETEROATOM LONE PAIRS [J].
PADWA, A ;
HORNBUCKLE, SF .
CHEMICAL REVIEWS, 1991, 91 (03) :263-309
[10]   Cascade processes of metallo carbenoids [J].
Padwa, A ;
Weingarten, MD .
CHEMICAL REVIEWS, 1996, 96 (01) :223-269