Dithiocarboxylation reactions of cis-bicyclo[3.3.0]octane-3,7-diones. Molecular and crystal structure of cis-2,6-bis(dimethylthiomethylene)-bicyclo[3.3.0]octane-3,7-dione

被引：1
作者：
Dolling, W
Siebel, HM
Biedermann, M
Hartung, H
机构：
[1] INST ORGAN CHEM, D-06120 HALLE, GERMANY
[2] INST PHYS CHEM, D-06108 HALLE, GERMANY
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 1996年 / 113卷 / 1-4期
关键词：
cis-bicyclo[3.3.0]octane-3,7-dione; cis-1,5-dimethylbicyclo[3.3.0]octane-3,7-dione; carbon disulfide; cis-2-(dialkylthio-methylene)-bicyclo[3.3.0]octane-3,7-dione; cis-2,6-bis(dimethylthio-methylene)-bicyclo[3.3.0]octane-3,7-dione; crystal structure;
D O I：
10.1080/10426509608046398
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The cis-bicyclo[3.3.0]octane-3,7-dione 1a and its 1,5-dimethyl derivative 1b react with carbon disulfide, strong base and an alkylating agent in dipolar aprotic solvents giving racemic mixtures of 2-dialkylthiomethylene compounds 2, whereas in the presence of two equivalents of carbon disulfide and the appropriate amount of basel and further alkylating agent the cis-2,6-bis(dimethylthio-methylene) derivatives 3 are formed. The crystal and molecular structure of 3a has been investigated by X-ray analysis.
引用
收藏
页码：263 / 274
页数：12
相关论文
共 23 条
[1]   TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[2]   On the effects of sulphur carbons and etch potash on ketones. [J].
Apitzch, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1905, 38 :2888-2899
[3]   The effect of carbon disulphide and potassium hydroxide on ketones. [J].
Apitzsch, H .
BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1908, 41 :4028-4039
[4]  
BERTZ SH, 1986, ORG SYNTH, V64, P27
[5]   VAN DER WAALS VOLUMES + RADII [J].
BONDI, A .
JOURNAL OF PHYSICAL CHEMISTRY, 1964, 68 (03) :441-+
[6]   STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-GYMNOMITROL VIA REDUCTION-ALKYLATION OF ALPHA-CYANO KETONES [J].
COATES, RM ;
SHAH, SK ;
MASON, RW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (08) :2198-2208
[7]   SYNTHESIS AND CRYSTAL-STRUCTURE OF S-(1-BENZOYL-2-BIS-METHYLTHIO)-VINYL-PIPERIDINO-DITHIOCARBAMATE [J].
DOLLING, W ;
KHOUDARY, K ;
AUGUSTIN, M ;
BAUMEISTER, U ;
HARTUNG, H .
TETRAHEDRON, 1988, 44 (14) :4399-4406
[8]   SYNTHESIS OF NEW KETENEDITHIOACETALS FROM N-CYANOMETHYL-2,2,N-TRIMETHYLPROPIONAMIDE, N-CYANOMETHYL-N-METHYLBENZAMIDE AND 4,4-DIMETHYL-3-OXOPENTANENITRILE AND CARBON-DISULFIDE [J].
DOLLING, W .
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1994, 86 (1-4) :129-137
[9]   VINYLSILANE MEDIATED STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)-GYMNOMITROL [J].
HAN, YK ;
PAQUETTE, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (21) :3731-3733
[10]   STRUCTURE OF (1S-STAR,5S-STAR,SR-STAR)-1-(3-PARA-TOLUENESULFINYL-2-PROPENYL)-2-METHYLENE-7,7-DIMETHYLBICYCLO[3.3.0]OCTAN-3-ONE [J].
HUA, DH ;
BADEJO, I ;
MCCANN, PJ ;
TAKUSAGAWA, F .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1987, 43 :1112-1114
123