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Behavior of protonated cyclopropyl intermediates during polyalphaolefin synthesis: Mechanism and predicted product distribution
Author(s) -
Gee Jeffrey C.,
Small Brooke L.,
Hope Kenneth D.
Publication year - 2012
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3059
Subject(s) - chemistry , carbocation , protonation , cationic polymerization , product distribution , electrophile , reaction mechanism , computational chemistry , stereochemistry , medicinal chemistry , photochemistry , organic chemistry , catalysis , ion
A new mechanism for the origin of multiple skeletal isomers observed in the cationic dimerization of 1‐decene is proposed, and products that should form based on this mechanism are predicted. A protonated cyclopropyl intermediate appeared to form directly from combination of 2‐decyl carbocation with 1‐decene; formation of this intermediate did not appear to occur via ring closure of a branched secondary carbocation. The authors propose that rapid, repeated isomerizations of the protonated cyclopropyl intermediates lead to multiple skeletal isomers in decene dimers. The proposed mechanism can account for structures previously identified in mixtures of decene dimers and butene dimers. Copyright © 2012 John Wiley & Sons, Ltd.