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Katalytische Hydrierung einiger Kohlenwasserstoffe mit spiroanellierten Bicyclopropyleinheiten
Author(s) -
Kaufmann Dieter,
de Meijere Armin
Publication year - 1983
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19831160241
Subject(s) - chemistry , cyclopropane , catalysis , medicinal chemistry , double bond , hexane , organic chemistry , ring (chemistry)
Catalytic Hydrogenation of Some Hydrocarbons with Spiroanellated Bicyclopropyl Units The spirocyclopropyl groups of dispiro[2.0.2.4]dec‐8‐ene ( 1 ) and dispiro[cyclopropane‐1,2′‐bicyclo[2.2.0]hexane‐3′, 1″‐cyclopropane] ( 11 ) both upon catalytic hydrogenation are ringopened to ethyl groups rather than gem ‐dimethyl groups as would be expected from literature precedents. The unusual behaviour is caused by a so‐called anchor effect, i. e. preferred adsorption on the catalyst's surface occurs at the site of the CC double bond in 1 and the most highly strained CC single bond in 11 respectively thereby determing the rate and direction of hydrogen addition to the cyclopropyl bonds.