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
[1]   BASE-CATALYZED HEMITHIOACETAL DECOMPOSITION AT A DIFFUSION-CONTROLLED RATE [J].
BARNETT, R ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (23) :5963-&
[2]   COMPARISON OF THE PHOTOOXIDATIONS OF 1,5-DITHIACYCLOOCTANE, 1,4-DITHIANE, AND PENTAMETHYLENE SULFIDE - ANOTHER EXAMPLE OF REMOTE PARTICIPATION DURING PHOTOOXIDATION AT SULFUR [J].
CLENNAN, EL ;
WANG, DX ;
YANG, K ;
HODGSON, DJ ;
OKI, AR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (08) :3021-3027
[3]  
FUJITA E, 1978, CHEM PHARM BULL, V26, P3743
[4]  
GARCIA H, 1989, NEW J CHEM, V13, P805
[5]   MECHANISMS FOR ENFORCED GENERAL ACID CATALYSIS OF ADDITION OF THIOL ANIONS TO ACETALDEHYDE [J].
GILBERT, HF ;
JENCKS, WP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1977, 99 (24) :7931-7947
[6]   ANODIC-OXIDATION OF DIALKYL AND DIARYL DITHIOACETALS [J].
GOURCY, J ;
MARTIGNY, P ;
SIMONET, J ;
JEMINET, G .
TETRAHEDRON, 1981, 37 (08) :1495-1502
[7]   STUDIES ON TOTAL SYNTHESIS OF OLIVOMYCINS [J].
HATCH, RP ;
SHRINGARPURE, J ;
WEINREB, SM .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (21) :4172-4177
[8]  
HOSHINO O, 1979, CHEM PHARM BULL, V27, P538
[9]   PHOTOINDUCED SINGLE ELECTRON-TRANSFER REACTIONS OF 1,3-DITHIANES AND 1,3-DITHIOLANES SENSITIZED BY TRIPHENYLPYRYLIUM SALT IN THE PRESENCE OF MOLECULAR-OXYGEN [J].
KAMATA, M ;
KATO, Y ;
HASEGAWA, E .
TETRAHEDRON LETTERS, 1991, 32 (34) :4349-4352
[10]  
PAGE PCB, 1989, TETRAHEDRON, V45, P7643