QUANTITATIVE-ANALYSES OF THE 4 ISOMERS OF 3,4-DIPHENYLCYCLOPENTENE BY CHIRAL GAS-CHROMATOGRAPHY

被引:16
作者
ASUNCION, LA [1 ]
BALDWIN, JE [1 ]
机构
[1] SYRACUSE UNIV,DEPT CHEM,SYRACUSE,NY 13244
关键词
D O I
10.1021/jo00123a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The four isomers of 3,4-diphenylcyclopentene are well resolved by chiral gas chromatography on a Cyclodex B column, eluting in the ordered sequence (3S,4R), (3R,4S), (3S,4S), and(3R,4R). Absolute stereochemical assignments were made through chemical correlations relating the 3,4-diphenylcyclopentenes with a known reference compound, (1S,2S)-(+)-cis-2-phenylcyclopentanol.
引用
收藏
页码:5778 / 5784
页数:7
相关论文
共 68 条
[1]   REACTIVITY OF EPOXIDES .3. METHODS FOR SYNTHESIS OF "1-HYDROXYALKYL-2-VINYLCYCLOPROPANES - REACTION OF GAMMA-DELTA-ETHYLENIC EPOXIDES WITH LITHIUM AMIDES IN HMPT [J].
APPARU, M ;
BARRELLE, M .
TETRAHEDRON, 1978, 34 (11) :1691-1697
[2]   STEREOCHEMISTRY OF THE THERMAL-ISOMERIZATION OF VINYLCYCLOPROPANE TO CYCLOPENTENE [J].
BALDWIN, JE ;
VILLARICA, KA ;
FREEDBERG, DI ;
ANET, FAL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (23) :10845-10846
[3]   STEREOCHEMICAL KINETICS OF THE THERMAL STEREOMUTATIONS OF 1-CYANO-2-PHENYL-1,3-DIDEUTERIOCYCLOPROPANES [J].
BALDWIN, JE ;
CARTER, CG .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (22) :3912-3917
[4]   STEREOCHEMISTRY OF THE THERMAL ISOMERIZATIONS OF (1R,2S)-1-(E-1-PROPENYL)-2-PHENYLCYCLOPROPANE TO 3-METHYL-4-PHENYLCYCLOPENTENES [J].
BALDWIN, JE ;
BONACORSI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (24) :7401-7409
[5]  
BODEN RM, 1975, SYNTHESIS-STUTTGART, P784
[6]  
BOLESOV IG, 1969, J ORG CHEM USSR, V5, P371
[7]  
BOLESOV IG, 1969, J ORG CHEM USSR, V5, P1665
[8]   HYDROBORATION .9. HYDROBORATION OF CYCLIC AND BICYCLIC OLEFINS-STEREOCHEMISTRY OF HYDROBORATION REACTION [J].
BROWN, HC ;
ZWEIFEL, G .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1961, 83 (11) :2544-&
[9]   ORGANOBORANES FOR SYNTHESIS .2. OXIDATION OF ORGANOBORANES WITH ALKALINE HYDROGEN-PEROXIDE AS A CONVENIENT ROUTE FOR THE CIS-HYDRATION OF ALKENES VIA HYDROBORATION [J].
BROWN, HC ;
SNYDER, C ;
RAO, BCS ;
ZWEIFEL, G .
TETRAHEDRON, 1986, 42 (20) :5505-5510
[10]   Anionotropic and prototropic changes an cyclic systems Part VI Cis- and trans-3 4-diphenylcyclopentanones - The structure of the ketone obtained by reduction of 2-hydroxy-3 4-daphenyl-Delta(2)-cyclopentenone with hydriodic acid [J].
Burton, H ;
Shoppee, CW .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :567-573