The isomerization chlorination of O,O-dialkyl methylthiophosphonates with phosphorus oxychloride - A new convenient synthesis of S-alkyl methylthiophosphonic acid derivatives

被引：12
|
作者：
Tang, CC
Ma, FP
Zhang, K
He, ZJ
Jin, YC
机构：
[1] Institute of Elemento-Organic Chemistry, Nankai University, Tianjin
来源：
HETEROATOM CHEMISTRY | 1995年 / 6卷 / 05期
关键词：
D O I：
10.1002/hc.520060506
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A new method for the synthesis of S-alkyl methylthiophosphonic acid derivatives is reported. The chlorination of O,O-dialkyl methylthiophosphonates 8 with phosphorus oxychloride proceeds with isomerization of the P = S to the P-S bond to give S-alkyl methylthiophosphonochloridates 9, which react further with various nucleophiles in the presence of triethylamine to afford S-alkyl methylthiophosphonic acid derivatives 10. Among them, several compounds 10 show excellent fungicidal or insecticidal activities. (C) 1995 John Wiley & Sons, Inc.
引用
收藏
页码：413 / 417
页数：5
相关论文
共 29 条
  • [1] The isomerization/chlorination of nitrogen heterocyclic O,O-dialkyl thiophosphoramidates with phosphorus oxychloride - A convenient synthesis of nitrogen heterocyclic S-alkyl thiophosphoramidic acid derivatives
    Tang, CC
    Lang, HF
    He, ZJ
    [J]. HETEROATOM CHEMISTRY, 1996, 7 (03) : 207 - 210
  • [2] The isomerization/chlorination of O,O-dialkyl N,N-dialkyl thiophosphoramidate with phosphorus oxychloride - A new method for synthesis of S-alkyl N,N-dialkyl thiophosphoramidic acid derivatives
    Tang, CC
    Wu, GP
    He, SJ
    He, ZJ
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1995, 101 (1-4): : 91 - 94
  • [3] THE ISOMERIZATION CHLORINATION OF O,O-DIALKYL-PHENYLTHIOPHOSPHONATES WITH PHOSPHORUS OXYCHLORIDE - A NEW CONVENIENT SYNTHESIS OF S-ALKYL-PHENYLTHIOPHOSPHONIC ACID-DERIVATIVES
    TANG, CC
    WU, GP
    HUANG, GY
    LI, Z
    JIN, GY
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 84 (1-4): : 159 - 164
  • [4] The Isomerization/Chlorination of O,O-Diallyl Thiophosphoric (-nic) Acid Esters with Phosphorus Oxychloride─A New Convenient Method for Synthesis of S-Alkyl Thiophosphoric(-nic) Acid Derivatives
    Zheng Jie HE
    Ju Xiang LIU
    Zheng Hong ZHOU
    and Chu Chi TANG(State Key Laboratory of Elemento-Organic Chemistry
    [J]. Chinese Chemical Letters, 1998, (10) : 903 - 905
  • [5] The isomerization/chlorination of O,O-diallyl thiophosphoric(-nic) acid esters with phosphorus oxychloride - A new convenient method for synthesis of S-alkyl thiophosphoric(-nic) acid derivatives
    He, ZJ
    Liu, JX
    Zhou, ZH
    Tang, CC
    [J]. CHINESE CHEMICAL LETTERS, 1998, 9 (10) : 903 - 905
  • [6] Direct α-chlorination of O,O-dialkyl chalcogenophosphonates with phosphorus oxychloride
    Mons, S
    Sabourault, N
    Klein, E
    Mioskowski, C
    Lebeau, L
    [J]. TETRAHEDRON LETTERS, 2001, 42 (43) : 7547 - 7549
  • [7] The chlorination reaction of O-alkyl S-alkyl(aryl) thiophosphoric(-nic) acid derivatives with phosphorus oxychloride
    He, ZJ
    Chen, WB
    Ma, FP
    Zhou, ZH
    Tang, CC
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 142 : 49 - 55
  • [8] The chlorination of O-alkyl S-alkyl(aryl) thiophosphoric(-nic) acids derivatives with phosphorus oxychloride -: A new method for synthesis of S-alkyl(aryl) thiophosphoro(-no)chloridates
    He, ZJ
    Chen, WB
    Ma, FP
    Zhou, ZH
    Tang, CC
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 1999, 20 (01): : 54 - 58
  • [9] A NEW CONVENIENT SYNTHESIS OF S-ALKYL N,N-DIALKYL THIOPHOSPHORAMIDIC ACID DERIVATIVES
    Chu Chi TANG Gui Ping WU Institute of Elemento-Organic Chemistry
    [J]. Chinese Chemical Letters, 1992, (08) : 593 - 594
  • [10] A CONVENIENT SYNTHESIS OF S-ALKYL O-ARYL THIOPHOSPHORIC ACID-DERIVATIVES
    TANG, CC
    WU, GP
    ZHANG, GZ
    [J]. SYNTHESIS-STUTTGART, 1991, (06): : 454 - 456
123