SYNTHESES OF [1-(ALKYLTHIO)]-AND (1-MERCAPTO) CYCLOALKANEPHOSPHONIC ESTERS BY REACTIONS OF CYCLOALKANETHIONES WITH TRIALKYL PHOSPHITES

被引:19
作者
YONEDA, S [1 ]
KAWASE, T [1 ]
YOSHIDA, Z [1 ]
机构
[1] KYOTO UNIV,DEPT SYNTHET CHEM,KYOTO 606,JAPAN
关键词
D O I
10.1021/jo00404a029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Cycloalkanethiones reacted with trialkyl phosphites to give [1-(alkylthio)]- and/or (1-mercapto)cycloalkanephosphonic esters. The reaction mechanism is discussed in terms of a concerted one via the betaine intermediate. These sulfur-containing esters are easily converted to cycloalkanephosphonic esters in good yields by Raney nickel treatment. © 1978, American Chemical Society. All rights reserved.
引用
收藏
页码:1980 / 1985
页数:6
相关论文
共 30 条
[1]   TRIALKYL PHOSPHITES - NOVEL RING-OPENING REACTIONS WITH DIMETHYLKETENE DIMERS [J].
BENTRUDE, WG ;
WITT, ER .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (16) :2522-&
[2]   STEREOSPECIFIC SYNTHESES OF OLEFINS FROM 1,2-THIONOCARBONATES AND 1,2-TRITHIOCARBONATES . TRANS-CYCLOHEPTENE [J].
COREY, EJ ;
CAREY, FA ;
WINTER, RAE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (04) :934-&
[3]  
COREY EJ, 1967, TETRAHEDRON LETT, P3201
[4]   A NEW, STEREOSPECIFIC OLEFIN SYNTHESIS FROM 1,2-DIOLS [J].
COREY, EJ ;
WINTER, RAE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (17) :2677-&
[5]   Concerning the mechanism of the reaction of trisubstituted Phosphines with episulfides [J].
Denney, Donald B. ;
Boskin, Marvin J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (17) :4736-4738
[6]   STUDIES IN ORGANIC SULFUR COMPOUNDS .11. REACTION OF ENAMINES WITH HYDROGEN SULFIDE [J].
DJERASSI, C ;
TURSCH, B .
JOURNAL OF ORGANIC CHEMISTRY, 1962, 27 (03) :1041-&
[7]  
DUUS F, ORGANIC COMPOUNDS SU, V3, P219
[8]  
DUUS F, ORGANIC COMPOUNDS SU, V2, P200
[9]   CHEMISTRY OF DIMETHYLKETENE DIMER .7. DIMERS OF DIMETHYLTHIOKETENE [J].
ELAM, EU ;
DAVIS, HE .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (05) :1562-&
[10]  
FORDMOORE AH, 1963, ORG SYNTH, V4, P955