Hypervalent iodine-induced multi-component reactions: Novel thiocyano- and isothiocyano-phenylselenenylating reaction of alkenes

被引:0
作者
Margarita, R
Mercanti, C
Parlanti, L
Piancatelli, G
机构
[1] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy
[2] Univ Roma La Sapienza, Ctr CNR Studio Chim Sostanze Organ Nat, I-00185 Rome, Italy
关键词
alkenes; iodine; selenium; sulfur; isothiocyanates; thiocyanates;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple and efficient thiocyano- or isothiocyano-phenylselenenylation of alkenes has been developed. The reactions occur when alkenes are treated with [bis(acetoxy)iodo]benzene, trimethylsilyl isothiocyanate or potassium thiocyanate and diphenyl diselenide. Mono- and disubstituted alkenes led to the formation of 1,2-phenylseleno-thiocyanates, whereas both more-substituted alkenes and styrenes gave exclusively 1,2-phenylseleno-isothiocyanates. The overall transformation represents the addition of PhSeSCN to the olefinic double bonds, in situ generated by the above reagents combination.
引用
收藏
页码:1865 / 1870
页数:6
相关论文
共 40 条
[1]  
ARNOLD JT, 1995, CANCER RES, V55, P537
[2]  
ATKINSON RN, 1998, 216 ACS NAT M
[3]   Asymmetric carbolithiation of 2-phenylselenofumarate derivatives: a short synthesis of (-)-roccellaric acid [J].
Bella, M ;
Margarita, R ;
Orlando, C ;
Orsini, M ;
Parlanti, L ;
Piancatelli, G .
TETRAHEDRON LETTERS, 2000, 41 (04) :561-565
[4]   OXIDATION OF DIPHENYL DISELENIDE WITH CERIC AMMONIUM-NITRATE - A NOVEL ROUTE FOR FUNCTIONALIZATION OF OLEFINS [J].
BOSMAN, C ;
DANNIBALE, A ;
RESTA, S ;
TROGOLO, C .
TETRAHEDRON LETTERS, 1994, 35 (35) :6525-6528
[5]   Hypervalent iodine chemistry: Novel and direct thiocyanation of alkenes using [bis(acetoxy)iodo]benzene/trimethylsilyl isothiocyanate reagent combination. Synthesis of 1,2-dithiocyanates. [J].
Bruno, M ;
Margarita, R ;
Parlanti, L ;
Piancatelli, G ;
Trifoni, M .
TETRAHEDRON LETTERS, 1998, 39 (22) :3847-3848
[6]   Strong hydrogen bond-mediated complexation of H2PO4- by neutral bis-thiourea hosts [J].
Buhlmann, P ;
Nishizawa, S ;
Xiao, KP ;
Umezawa, Y .
TETRAHEDRON, 1997, 53 (05) :1647-1654
[7]   Vinylic selenides and tellurides - Preparation, reactivity and synthetic applications [J].
Comasseto, JV ;
Ling, LW ;
Petragnani, N ;
Stefani, HA .
SYNTHESIS-STUTTGART, 1997, (04) :373-&
[8]  
DELAQUIS PJ, 1975, FOOD TECHNOLOGY, P73
[9]   A versatile and highly selective hypervalent iodine (III)/2,2,6,6-tetramethyl-1-piperidinyloxyl-mediated oxidation of alcohols to carbonyl compounds [J].
DeMico, A ;
Margarita, R ;
Parlanti, L ;
Vescovi, A ;
Piancatelli, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (20) :6974-6977
[10]  
DeMico A, 1997, CHEM COMMUN, P1237