Design, synthesis, application and recovery of a minimally fluorous diaryl diselenide for the catalysis of stannane-mediated radical chain reactions

被引:36
作者
Crich, D [1 ]
Hao, XL [1 ]
Lucas, M [1 ]
机构
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
基金
美国国家科学基金会;
关键词
radicals and radical reactions; catalysis; selenium and compounds; fluorine and compounds;
D O I
10.1016/S0040-4020(99)00902-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a minimally fluorous (52% F) diaryl diselenide is described. On reduction in situ with tributylstannane this diselenide provides a fluorous selenol which is effective in inhibiting a range of stannane-mediated radical rearrangements, including a cyclopropylcarbinyl ring opening. A method for the recovery of the fluorous diselenide involving continuous extraction in a modified, cooled continuous extractor is described. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:14261 / 14268
页数:8
相关论文
共 38 条
[1]   CONSECUTIVE RING-CLOSURE AND NEOPHYL REARRANGEMENT OF SOME ALKENYLARYL RADICALS [J].
ABEYWICKREMA, AN ;
BECKWITH, ALJ ;
GERBA, S .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (18) :4072-4078
[2]   KINETICS AND MECHANISM OF SOME VINYL RADICAL CYCLIZATIONS [J].
BECKWITH, ALJ ;
OSHEA, DM .
TETRAHEDRON LETTERS, 1986, 27 (38) :4525-4528
[3]   Chemistry of β-(acyloxy)alkyl and β-(phosphatoxy)alkyl radicals and related species:: Radical and radical ionic migrations and fragmentations of carbon-oxygen bonds [J].
Beckwith, ALJ ;
Crich, D ;
Duggan, PJ ;
Yao, QW .
CHEMICAL REVIEWS, 1997, 97 (08) :3273-3312
[4]  
CERNY V, 1973, COLLECT CZECH CHEM C, V38, P565
[5]   RATE CONSTANTS AND ARRHENIUS PARAMETERS FOR THE REACTIONS OF PRIMARY, SECONDARY, AND TERTIARY ALKYL RADICALS WITH TRI-NORMAL-BUTYLTIN HYDRIDE [J].
CHATGILIALOGLU, C ;
INGOLD, KU ;
SCAIANO, JC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (26) :7739-7742
[6]   USE OF RADICAL RING-OPENING FOR INTRODUCTION OF ALKYL AND SUBSTITUTED ALKYL-GROUPS WITH STEREOCHEMICAL CONTROL - A SYNTHETIC APPLICATION OF CYCLOPROPYLCARBINYL RADICALS [J].
CLIVE, DLJ ;
DAIGNEAULT, S .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12) :3801-3814
[7]   The beta-(Phosphatoxy)alkyl radical rearrangement. Rate constants, Arrhenius parameters, and structure activity relationships [J].
Crich, D ;
Jiao, XY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (28) :6666-6670
[8]   CHEMISTRY OF BETA-(PHOSPHATOXY)ALKYL AND BETA-(ACYLOXY)ALKYL RADICALS - MIGRATION REACTIONS - SCOPE AND STEREOSELECTIVITY OF BETA-(PHOSPHATOXY)ALKYL REARRANGEMENT - MECHANISM OF BETA-(PHOSPHATOXY)ALKYL AND BETA-(ACYLOXY)ALKYL MIGRATION [J].
CRICH, D ;
YAO, QW ;
FILZEN, GF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (46) :11455-11470
[9]   Radical clock reactions under pseudo-first-order conditions using catalytic quantities of diphenyl diselenide. A Se-77- and Sn-119-NMR study of the reaction of tributylstannane diphenyl diselenide [J].
Crich, D ;
Jiao, XY ;
Yao, QW ;
Harwood, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (07) :2368-2373
[10]   THE BETA-(PHOSPHONOOXY)ALKYL RADICAL REARRANGEMENT [J].
CRICH, D ;
YAO, QW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (03) :1165-1166