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The Ever‐Elusive Tetra‐ tert ‐butylethene (TTBE, 3,4‐Di‐ tert ‐butyl‐ 2,2,5,5‐tetramethylhex‐3‐ene): Further Insight on Its Preparation
Author(s) -
Klein Oliver,
Hopf Henning,
Grunenberg Jörg
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200801292
Subject(s) - chemistry , tetra , ene reaction , derivative (finance) , hydrolysis , ketone , furan , medicinal chemistry , diketone , alkylation , stereochemistry , organic chemistry , catalysis , financial economics , economics
Diketone 4 was prepared by hydrolysis of hexendiyne 5 , the latter being available through McMurry coupling of acetylenic ketone 26 . Upon treatment with dimethyltitanium dichloride, 4 cyclizes into fully alkylated furan derivative 30 ; the still unknown tetra‐ tert ‐butylethene ( 1 , TTBE, 3,4‐di‐ tert ‐butyl‐2,2,5,5‐tetramethylhex‐3‐ene) was not produced. The structural properties of 4 and the mechanism of its cyclization into 30 are discussed. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)