REACTION OF PHOSPHOLE SULFIDES WITH DIAZOALKANES AS A NEW ROUTE TO PHOSPHININES

被引：16
|
作者：
HOLAND, S [1 ]
RICARD, L [1 ]
MATHEY, F [1 ]
机构：
[1] ECOLE POLYTECH, DCPH, CHIM PHOSPHORE & MET TRANSIT LAB, F-91128 PALAISEAU, FRANCE
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 12期
关键词：
D O I：
10.1021/jo00012a042
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of ethyl diazoacetate with 1-(methylthio)-3,4-dimethylphosphole 1-sulfide (6) in refluxing xylene leads to the corresponding diene-carbene [2 + 1] cycloadduct 7. The sterochemistry of 7 was established by X-ray crystal structure analysis. Compound 7 is converted into 2-(ethoxycarbonyl)-4,5-dimethylphosphinine (4) upon reaction with triphenyl phosphite at 160-degrees-C. On the basis of the X-ray data, the proposed mechanism includes the opening of the cyclopropane ring of 7 with selective phosphorus-assisted migration of the ethoxycarbonyl group. This kind of chemistry can be transposed to a 2,2'-biphosphole to prepare a 2,2'-biphosphinine.
引用
收藏
页码：4031 / 4035
页数：5
相关论文
共 50 条
  • [31] REACTION OF LAMBDA-3-PHOSPHININES WITH DIPHENYLCARBENES FROM DIPHENYLDIAZOMETHANE
    MARKL, G
    HOHENWARTER, K
    ZIEGLER, ML
    NUBER, B
    TETRAHEDRON LETTERS, 1990, 31 (34) : 4849 - 4852
  • [32] THE REACTION OF SOME DIAZOALKANES WITH TRIALKYLSILYL(GERMYL)PROPYNALS
    MEDVEDEVA, AS
    DEMINA, MM
    BORISOVA, AI
    KALIKHMAN, ID
    VYAZANKIN, NS
    ZHURNAL OBSHCHEI KHIMII, 1981, 51 (06): : 1324 - 1328
  • [33] SYNTHESIS OF NITRONES BY REACTION OF ISONITROISOMALONIC ESTERS WITH DIAZOALKANES
    KOSTYANOVSKII, RG
    MARKOV, VI
    MISHCHENKO, AI
    PROSYANIK, AV
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1977, 26 (01): : 224 - 225
  • [34] Reaction of quinones with diazoalkanes and some synthetic application
    Kokubo, K
    Oshima, T
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2003, 61 (04) : 360 - 369
  • [35] THE REACTION OF TERMINAL PHOSPHINIDENE COMPLEXES WITH ELECTRON-RICH ALKYNES - A NEW APPROACH TO THE PHOSPHOLE RING
    HUY, NHT
    MATHEY, F
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1990, 47 (3-4) : 477 - 481
  • [36] TBAI-catalyzed oxidative C-H functionalization: a new route to benzo[b]phosphole oxides
    Zhang, Yun
    Hu, Gaobo
    Ma, Dumei
    Xu, Pengxiang
    Gao, Yuxing
    Zhao, Yufen
    CHEMICAL COMMUNICATIONS, 2016, 52 (13) : 2815 - 2818
  • [37] NEW ROUTE TO (Z)-ALLYLIC SULFIDES VIA A 10-MEMBERED THIOLCARBONATE
    HARUSAWA, S
    KUROKAWA, T
    FUJII, H
    YONEDA, R
    KURIHARA, T
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (09) : 2567 - 2569
  • [38] The Generation of (Samarium) Thiolates From Aryl Thiocyanates and their Reaction with Epoxides: A Route to QQ -Hydroxy Sulfides
    Still, I. W. J.
    Martyn, L. J. P.
    Synthetic Communications, 28 (05):
  • [39] REACTION OF NITROPRUSSIDE WITH SULFIDES AND PHOTOMETRIC DETERMINATION OF SULFIDES
    TOROPOVA, VF
    RYBKINA, AA
    ZHURNAL ANALITICHESKOI KHIMII, 1973, 28 (07): : 1355 - 1359
  • [40] A Route to α-Fluoroalkyl Sulfides from α-Fluorodiaroylmethanes
    Lin, Ya-mei
    Yi, Wen-bin
    Shen, Wan-zhao
    Lu, Guo-ping
    ORGANIC LETTERS, 2016, 18 (03) : 592 - 595
12345