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.
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页码:1865 / 1870
页数:6
相关论文
共 40 条
[11]   ALLYLSELENIDES POSSESSING A TERMINAL DOUBLE-BOND 1ST REGIOSELECTIVE SYNTHESIS AND REACTIONS [J].
DIGIAMBERARDINO, T ;
HALAZY, S ;
DUMONT, W ;
KRIEF, A .
TETRAHEDRON LETTERS, 1983, 24 (32) :3413-3416
[12]   The chemistry of thiocyanic esters [J].
Erian, AW ;
Sherif, SM .
TETRAHEDRON, 1999, 55 (26) :7957-8024
[13]   Hypervalent iodine chemistry: Mechanistic investigation of the novel haloacetoxylation, halogenation, and acetoxylation reactions of 1,4-dimethoxynaphthalenes [J].
Evans, PA ;
Brandt, TA .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (16) :5321-5326
[14]   Novel haloacetoxylation of 1,4-dimethoxynaphthalenes using hypervalent iodine chemistry [J].
Evans, PA ;
Brandt, TA .
TETRAHEDRON LETTERS, 1996, 37 (36) :6443-6446
[15]   MOLECULAR RECOGNITION - HYDROGEN-BONDING RECEPTORS THAT FUNCTION IN HIGHLY COMPETITIVE SOLVENTS [J].
FAN, E ;
VANARMAN, SA ;
KINCAID, S ;
HAMILTON, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :369-370
[16]   SELENENYL SULFUR COMPOUNDS [J].
FOSS, O .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (09) :2236-2237
[17]   4,5,6,7-TETRAHYDROXYDECYL ISOTHIOCYANATE DERIVED FROM A GLUCOSINOLATE IN CAPPARIS-GRANDIS [J].
GAIND, KN ;
GANDHI, KS ;
JUNEJA, TR ;
KJAER, A ;
NIELSEN, BJ .
PHYTOCHEMISTRY, 1975, 14 (5-6) :1415-1418
[18]   CHEMOSELECTIVITY IN THE SYNTHESIS OF THIOCYANATES AND ISOTHIOCYANATES - REACTION OF ALKENES WITH BENZENESELENENYL THIOCYANATE IN METHYLENE-CHLORIDE [J].
GARRATT, DG ;
RYAN, MD ;
UJJAINWALLA, M .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2145-2153
[19]   REACTION OF BENZENESELENENYL THIOCYANATE WITH E-1-PHENYLPROPENE AND Z-1-PHENYLPROPENE - EVIDENCE FOR ANOMALOUS STEREOSPECIFIC SYN ADDITION [J].
GARRATT, DG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2180-2184
[20]  
Guy R. G., 1977, CHEM CYANATES THEIR