Preferred syn-elimination from trans-1,2-dichloro- and trans-1,2-dibromocyclodecane

syn-Coplanar cleavage of hydrogen halide, esp. the syn -> trans process, was favored in the dehydrohalogenation of trans-1,2-dichlorocyclodecane and trans-1,2-dibromocyclodecane, and the anti elimination, which was most favored with acyclic compds., was retarded. The transition state for syn elimination was thought to be stabilized by redn. in transannular repulsive forces. The dehydrohalogenation rate depended only slightly on the solvent. [on SciFinder (R)]


Published in:
Angewandte Chemie, International Edition in English, 10, 12, 926-7
Year:
1971
Keywords:
Note:
CAN 76:58836 22 Physical Organic Chemistry Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0570-0833 written in English. 21652-97-1; 29509-49-7 Role: RCT (Reactant), RACT (Reactant or reagent) (dehydrohalogenation of, stereochemistry of); 34949-20-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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