The syn-anti ratio of 7-(R-substituted)-norcaranes (I, R = Ph. F, Cl) formed in the cycloaddn. of cyclohexene (II) with PhCH2F, PhCH2Cl, PhCHBrF, PhCHBr2, FCHBr2, ClCHBr2, or CH2Cl and BuLi in various solvents under N was examd. with respect to influences on the stereoselectivity. II concn. was the strongest factor while the nature of org. halide, solvent, and Li halide formed influenced the selectivity also: syn-anti ratios 2.0-40.0 were obtained for (R = Ph) and 1.85-2.46 for I (R = halogen). I (R = Ph) rearranged to 2-benzyl-1-cyclohexene. [on SciFinder (R)]
Title
Die Beeinflußbarkeit der syn-Stereoselektivität bei Carben-Additionen an Olefine
Published in
Chemische Berichte
Volume
103
Issue
11
Pages
3543-3552
Date
1970
Note
CAN 74:12496 22 Physical Organic Chemistry Org.-Chem. Inst.,Univ. Heidelberg,Heidelberg,Fed. Rep. Ger. Journal 0009-2940 written in German. 100-44-7; 350-50-5 (Toluene, a-fluoro-); 618-31-5; 17815-88-2 Role: RCT (Reactant), RACT (Reactant or reagent) (cycloaddn. reaction of, with cyclohexene); 4714-10-7P; 31053-19-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 3101-08-4 Role: RCT (Reactant), RACT (Reactant or reagent) (reaction of, with cyclohexene); 110-83-8 Role: RCT (Reactant), RACT (Reactant or reagent) (with phenylcarbene, stereochemistry of)
Record creation date
2006-03-03
