Radical Cyanation of Alkyl Iodides with Diethylphosphoryl Cyanide

被引:9
作者
Cho, Chang Ho [1 ]
Lee, Jin Young [1 ]
Kim, Sunggak [1 ]
机构
[1] Korea Adv Inst Sci & Technol, Dept Chem, Sch Mol Sci BK 21, Taejon 305701, South Korea
关键词
radical; cyanide; elimination; alkyl halides; BETA-ELIMINATION; CARBONYL GROUP; ACYLPHOSPHONATE DERIVATIVES; CYCLIZATION REACTIONS; HYPOPHOSPHOROUS ACID; PHOSPHONATE GROUP; NITROGEN BONDS; TIN; AZIDATION; PSEUDOHALOGENATION;
D O I
10.1055/s-0028-1087385
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The beta-elimination of an organophosphoryl group from an iminyl radical is observed for the first time. On the basis of this finding, radical cyanation of alkyl iodides is achieved by using diethylphosphoryl cyanide.
引用
收藏
页码:81 / 84
页数:4
相关论文
共 47 条
[1]  
Baguley PA, 1998, ANGEW CHEM INT EDIT, V37, P3073, DOI 10.1002/(SICI)1521-3773(19981204)37:22<3072::AID-ANIE3072>3.0.CO
[2]  
2-9
[3]   THE INVENTION OF RADICAL REACTIONS .23. NEW REACTIONS - NITRILE AND THIOCYANATE TRANSFER TO CARBON RADICALS FROM SULFONYL CYANIDES AND SULFONYL ISOTHIOCYANATES [J].
BARTON, DHR ;
JASZBERENYI, JC ;
THEODORAKIS, EA .
TETRAHEDRON, 1992, 48 (13) :2613-2626
[4]   HYPOPHOSPHOROUS ACID AND ITS SALTS - NEW REAGENTS FOR RADICAL CHAIN DEOXYGENATION, DEHALOGENATION AND DEAMINATION [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
TETRAHEDRON LETTERS, 1992, 33 (39) :5709-5712
[5]   THE INVENTION OF RADICAL REACTIONS .32. RADICAL DEOXYGENATIONS, DEHALOGENATIONS, AND DEAMINATIONS WITH DIALKYL PHOSPHITES AND HYPOPHOSPHOROUS ACID AS HYDROGEN SOURCES [J].
BARTON, DHR ;
JANG, DO ;
JASZBERENYI, JC .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (24) :6838-6842
[6]   β Elimination of a phosphonate group from an alkoxyl radical -: Intramolecular acylation using acylphosphonate derivatives as carbonyl group acceptors [J].
Cho, CH ;
Kim, S .
CANADIAN JOURNAL OF CHEMISTRY, 2005, 83 (6-7) :917-921
[7]   Radical cyclizations of alkenyl acylphosphonate derivatives under thermal and photochemical conditions [J].
Cho, CH ;
Kim, S ;
Yamane, M ;
Miyauchi, H ;
Narasaka, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2005, 78 (09) :1665-1672
[8]   Synthesis of biaryls by intramolecular radical transfer: use of phosphinates [J].
Clive, DLJ ;
Kang, SZ .
TETRAHEDRON LETTERS, 2000, 41 (09) :1315-1319
[9]  
Coskran K.J., 1971, Inorg. Chem, V10, P1536
[10]  
CURRAN DP, 1992, SYNLETT, P631