Convenient one-pot synthesis of 4,8-dimethyl-bicyclo[3.3.1]non-7-en-2-ol via platinum/tin catalyzed hydroformylation/cyclization of limonene

被引:32
作者
Dias, AD [1 ]
Augusti, R [1 ]
dos Santos, EN [1 ]
Gusevskaya, EV [1 ]
机构
[1] UNIV FED MINAS GERAIS, DEPT QUIM, ICEX, BR-31270901 BELO HORIZONTE, MG, BRAZIL
关键词
D O I
10.1016/S0040-4039(96)02251-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Limonene (1) was converted in one step into two diasteroisomers of 4,8-dimethyl-bicyclo[3.3.1]non-7-en-2-ol (2), useful as perfumes, employing PtCl2(PPh(3))(2)/PPh(3)/SnCl2 and PtCl2(diphosphine)/PPh(3)/SnCl2 systems as bifunctional catalysts whose diphosphines were 1,3-bis(diphenylphosphino)propane (dppp) and 1,4-bis(diphenylphosphino)butane (dppb). In the presence of the PtCl2(dppb)/PPh(3)/SnCl2 system, which was found to be the most promising combination,the selectivity for 2 reached the value of 82% at 95% conversion of 1. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:41 / 44
页数:4
相关论文
共 8 条
  • [1] [Anonymous], CATALYSIS ORGANIC RE
  • [2] AUGUSTI R, 1995, P 8 SEM BRAS CAT NOV, P360
  • [3] Barbieri R, 1991, QUIM NOVA, V14, P212
  • [4] CARBON-MONOXIDE AS A BUILDING BLOCK FOR ORGANIC-SYNTHESIS .3. SELECTIVE HYDROCARBONYLATION OF MONOTERPENES TO GIVE POTENTIALLY BIOLOGICALLY-ACTIVE ALDEHYDES
    CIPRES, I
    KALCK, P
    PARK, DC
    SEREINSPIRAU, F
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1991, 66 (03): : 399 - 407
  • [5] PLATINUM CHLORIDE-DIPHOSPHINE-TIN(II) HALIDE-SYSTEMS AS ACTIVE AND SELECTIVE HYDROFORMYLATION CATALYSTS
    HAYASHI, T
    KAWABATA, Y
    ISOYAMA, T
    OGATA, I
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (11) : 3438 - 3446
  • [6] HYDROFORMYLATION OF CHIRAL TERPENES WITH PTCL(SNCL3)-(BIS-PHOSPHINE) AS CATALYST
    KOLLAR, L
    BAKOS, J
    HEIL, B
    SANDOR, P
    SZALONTAI, G
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 385 (01) : 147 - 152
  • [7] 60100532
  • [8] 59112933