Acetyl chloride-mediated synthesis of trans-2-[(diethoxyphosphorylamino)alkyl]-4-aryl-5,5-dimethyl-1,3,2λ5-dioxaphosphorinane-2-oxide

被引:4
|
作者
Miao, Zhiwei [1 ]
Zhang, Jianfeng [1 ]
Cui, Zhanwei [1 ]
Chen, Ruyu [1 ]
机构
[1] Nankai Univ, Res Inst Elementoorgan Chem, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
关键词
D O I
10.1246/bcsj.81.630
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
N-Phosphoramino-protected six-membered cyclic alpha-aminophosphonates trans-2-[(diethoxyphosphorylamino)-alkyll-4-aryl-5,5-dimethyl-1,3,2 lambda(5)-dioxaphosphorinane-2-oxide 4a-4l were synthesized with the help of acetyl chloride. (PNMR)-P-31 was used to trace the reaction process. A possible reaction mechanism was proposed and the stereochemistry of the title compounds was studied. In order to confirm the structure of 4, products 4f and 4k were recrystallized and determined by X-ray diffraction analysis.
引用
收藏
页码:630 / 635
页数:6
相关论文
共 50 条
  • [1] Synthesis of 2-substituted-5,5-dimethyl-1,3,2-dioxaphosphorinane-2-oxides
    Raghu, KV
    Reddy, CD
    Raju, CN
    ASIAN JOURNAL OF CHEMISTRY, 1996, 8 (01) : 45 - 48
  • [2] THERMAL INTRAMOLECULAR ISOMERIZATION OF 2-ISOSELENOCYANO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE TO 2-CYANO-2-SELENO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE
    UZNANSKI, B
    STETS, VI
    ZHURNAL OBSHCHEI KHIMII, 1990, 60 (06): : 1225 - 1235
  • [3] 2-FORMYLAMINO-2-OXO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE
    CAMERON, TS
    KAROLAKWOJCIECHOWSKA, J
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (JUL15): : 2342 - 2344
  • [4] 2-SELENO-2-METHOXY-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE
    GRAND, A
    MARTIN, J
    ROBERT, JB
    TORDJMAN, I
    ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1975, 31 (OCT15): : 2523 - 2524
  • [5] Studies on the synthesis and biological activities of 2-[(2-chloro-5-pyridylmethylamino)(aryl)methyl]-4-aryl-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxides
    Sun, Feng-Mei
    Shi, De-Qing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (10) : 1398 - 1402
  • [6] Structural studies of the bisimidazole 5,5-dimethyl-1,3,2-dioxaphosphorinane-2-thioxo-2-hydroxy complex
    Potrzebowski, MJ
    Cypryk, M
    Michalska, M
    Koziol, AE
    Kazmierski, S
    Ciesielski, W
    Klinowski, J
    JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (23): : 4488 - 4494
  • [7] Interaction of 2-isocyanato-5,5-dimethyl-1,3,2-dioxaphosphorinane with nitrileimines
    Andreev, VV
    Chernyshova, NN
    Labeish, NN
    Galishev, VA
    ZHURNAL OBSHCHEI KHIMII, 1997, 67 (11): : 1827 - 1829
  • [8] STUDY OF 2-(1-IMIDAZOLYL)-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE
    NIFANTEV, EE
    GRACHEV, MK
    BEKKER, AR
    VASYANINA, LK
    KOROTEEV, AM
    ZHURNAL OBSHCHEI KHIMII, 1988, 58 (02): : 312 - 316
  • [9] CONFORMATIONAL EQUILIBRIUM OF 2-HYDRO-2-OXO-5,5-DIMETHYL-1,3,2-DIOXAPHOSPHORINANE
    MATROSOV, EI
    KRYUCHKOV, AA
    NIFANTEV, EE
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (11): : 2473 - 2474
  • [10] Six-membered cyclic phosphate-phosphonates:: synthesis and stereochemistry of cis/trans-2-phosphorylbenzyloxy-4-aryl-5,5-dimethyl-1,3,2λ5-dioxaphosphorinane-2-thiones (selones)
    Zhou, J
    Chen, RY
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (17): : 2917 - 2921