PHOTOSENSITIZED CLEAVAGE OF THE DITHIOPROTECTING GROUP BY VISIBLE-LIGHT

被引:27
作者
EPLING, GA
WANG, QX
机构
[1] Department of Chemistry, University of Connecticut, Storrs
关键词
ELECTRON TRANSFER; PHOTOFRAGMENTATION; DITHIANES; DITHIOLANES; PHOTOLYSIS;
D O I
10.1016/S0040-4039(00)61086-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dithio derivatives of aldehydes and ketones have been deprotected under neutral conditions using visible light provided by a 120 Watt spotlight and methylene green as a sensitizer. The key step in the deprotection is apparently an electron transfer from the dithio derivative to the electronically excited visible dye. The resulting dithio radical cation undergoes fragmentation, and the corresponding aldehydes and ketones are isolated in excellent yields.
引用
收藏
页码:5909 / 5912
页数:4
相关论文
共 18 条
[11]   EFFICIENT SYNTHETIC METHODOLOGY FOR 1,3-DITHIOLANE 1-OXIDES VIA SINGLET OXIDATION OF 1,3-DITHIOLANES [J].
PANDEY, B ;
BAL, SY ;
KHIRE, UR ;
RAO, AT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (11) :3217-3218
[12]   INDIRECT ELECTROCHEMICAL PROCESSES .15. MILD AND EFFECTIVE REMOVAL OF DITHIOKETAL PROTECTING GROUPS BY TRIARYLAMINE CATION RADICALS AS HOMOGENEOUS ELECTRON-TRANSFER AGENTS [J].
PLATEN, M ;
STECKHAN, E .
CHEMISCHE BERICHTE-RECUEIL, 1984, 117 (05) :1679-1694
[13]   EFFECTIVE AND MILD ELECTROCATALYTIC PROCEDURE FOR THE REMOVAL OF 1,3-DITHIANE PROTECTING GROUPS [J].
PLATEN, M ;
STECKHAN, E .
TETRAHEDRON LETTERS, 1980, 21 (06) :511-514
[14]   ELECTRO-ORGANIC REACTIONS .24. PREPARATIVE AND MECHANISTIC ASPECTS OF THE ANODIC-OXIDATION OF DITHIOACETALS AND 1,3-DITHIANES [J].
PORTER, QN ;
UTLEY, JHP ;
MACHION, PD ;
PARDINI, VL ;
SCHUMACHER, PR ;
VIERTLER, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :973-979
[15]  
PORTER QN, 1978, J CHEM SOC CHEM COMM
[16]  
REHM D, 1970, ISRAEL J CHEM, V8, P259
[17]   PHOTOOXIDATION OF 1,5-DITHIACYCLOOCTANE - A NOVEL C-S BOND-CLEAVAGE [J].
SHEU, CM ;
FOOTE, CS ;
GU, CL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3015-3021
[18]   NOVEL DETHIOACETALISATION BY PHOTOLYSIS [J].
TAKAHASHI, TT ;
NAKAMURA, CY ;
SATOH, JY .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1977, (19) :680-680