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Catalyzed dimerization of 2,5‐dimethyl‐2,4‐hexadiene. H‐ and 13 C‐NMR studies on exo ‐3‐isopropenyl‐ exo ‐6‐isopropyl‐1, endo ‐2,4,4‐tetramethylbicyclo[3.1.0]hexane
Author(s) -
Mattay Jochen,
Trampe Gisela,
Runsink Jan,
Meltzow Wilhelm,
Jans Arnold W. H.
Publication year - 1988
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.19881210925
Subject(s) - chemistry , dimer , isopropyl , lewis acids and bases , hexane , catalysis , stereochemistry , tris , brønsted–lowry acid–base theory , nmr spectra database , medicinal chemistry , nuclear magnetic resonance spectroscopy , organic chemistry , spectral line , biochemistry , physics , astronomy
2,5‐Dimethyl‐2,4‐hexadiene ( 1 ) dimerizes under Lewis acid catalysis or in the presence of tris(4‐bromophenyl)aminium hexachlorostibanate ( 4 ) mainly to give exo ‐3‐isopropenyl‐ exo ‐6‐isopropyl‐1, endo ‐2,4,4‐tetramethylbicyclo[3.1.0]hexane ( 2 ). Small amounts of the acyclic dimer 2,5,7,7,10‐pentamethyl‐2,4,8‐undecatriene ( 3 ) and traces of other unidentified dimeric and trimeric products are formed as well. The latter are the only products in the presence of Brønsted acids, whereas 2 and 3 were not detected under these conditions. The structural assignment of 2 has been carried out by means of 2D‐INADEQUATE, ‐HETCOR, and ‐COSY spectra.