C-BIFUNCTIONAL SILACYCLOPENTANES AND GERMACYCLOPENTANES .1. 1-SILACYCLOPENTAN-2,3-DIOLS AND 1-GERMACYCLOPENTAN-2,3-DIOLS AND 1-GERMACYCLOPENTAN-3,4-DIOLS

被引:14
作者
MANUEL, G
BOUKHERROUB, R
机构
关键词
D O I
10.1016/0022-328X(93)80235-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
C-bifunctional sila- and germacyclopentanes have some potential as biologically active drugs. Ten representative 1-sila (and 1-germa) cyclopentane-2,3 and 3,4-diols, cis or trans, were synthesized from the corresponding 1-metallacyclopen-3-enes. The influence of the metal, silicon or germanium, on each step leading to 3 sets of alpha-diols is underlined. The stereochemistry of the alpha-diols and their precursors was established by H-1 and C-13 NMR spectroscopy.
引用
收藏
页码:167 / 175
页数:9
相关论文
共 32 条
[1]   REACTION OF 6-OXA-3-SILABICYCLO[3.1.0]HEXANES WITH PHOSPHINIMINES - SYNTHESIS OF 6-VINYL-1,3-DIOXA-2,4-DISILACYCLOHEXANES [J].
BACEIREDO, A ;
JUENGST, CD ;
MANUEL, G ;
WEBER, WP .
CHEMISTRY LETTERS, 1987, (02) :237-240
[2]  
BENDZ G, 1978, BIOCH SILICON RELATE
[3]   EPOXIDATION OF ALLYLIC ALCOHOLS WITH PEROXY-ACIDS - ATTEMPTS TO DEFINE TRANSITION STATE GEOMETRY [J].
CHAMBERL.P ;
ROBERTS, ML ;
WHITHAM, GH .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (07) :1374-&
[4]   BASE-PROMOTED REACTIONS OF EPOXIDES .V. 1-ALKYLCYCLOALKENE OXIDES [J].
CRANDALL, JK ;
LIN, LHC .
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2375-&
[5]   BASE-PROMOTED REACTIONS OF EPOXIDES .I. ISOMERIZATION OF SOME CYCLIC AND ACYCLIC EPOXIDES BY LITHIUM DIETHYLAMIDE [J].
CRANDALL, JK ;
CHANG, LH .
JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (02) :435-&
[6]   GAS-PHASE NEGATIVE-ION CHEMISTRY OF 6-OXA-3-SILABICYCLO[3.1.0]HEXANE AND GERMABICYCLO[3.1.0]HEXANE [J].
DAMRAUER, R ;
WEBER, WP ;
MANUEL, G .
CHEMISTRY LETTERS, 1987, (02) :235-236
[7]   SYNTHESIS OF 3-METHYLENE-1,1-DICHLOROSILACYCLOBUTANE AND 1,1-DICHLOROSILACYCLOPENT-3-ENE [J].
DAMRAUER, R ;
SIMON, R ;
LAPORTERIE, A ;
MANUEL, G ;
PARK, YT ;
WEBER, WP .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1990, 391 (01) :7-12
[8]   KINETICS AND MECHANISM OF THE PYROLYSIS OF 6-OXA-3,3-DIMETHYL-3-SILABICYCLO[3.1.0]HEXANE, A DIMETHYLSILANONE PRECURSOR [J].
DAVIDSON, IMT ;
FENTON, A ;
MANUEL, G ;
BERTRAND, G .
ORGANOMETALLICS, 1985, 4 (08) :1324-1327
[9]   METALLOLES-14 CHEMISTRY [J].
DUBAC, J ;
LAPORTERIE, A ;
MANUEL, G ;
ILOUGHMANE, H .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1986, 27 (1-2) :191-203
[10]   NEW FORMATION OF SILICON-CARBON BONDS FROM CHLOROSILANES .6. DOUBLE SILYLATION OF 1,4-CONJUGATED DIENES [J].
DUNOGUES, J ;
CALAS, R ;
DEDIER, J ;
PISCIOTT.F .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1970, 25 (01) :51-&