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Preparation of Highly Hindered Polyenynes
Author(s) -
Kiliçkiran Pinar,
Hopf Henning,
Dix Ina,
Jones Peter G.
Publication year - 2010
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.201000018
Subject(s) - chemistry , reactivity (psychology) , diastereomer , steric effects , acetylene , thiophene , sodium sulfide , sulfide , organic chemistry , medicinal chemistry , stereochemistry , medicine , alternative medicine , pathology
The terminal enynes 10 – 12 were prepared from the corresponding aldehydes 6 – 8 by applying conventional methods of acetylene chemistry. After exploratory study of the reactivity of these hydrocarbons (preparation of 13 , 18 , and 19 from 10 ) these building blocks were subsequently oxidatively dimerized (Glaser coupling) to the sterically protected oligoenynes 22 – 25 ; McMurry coupling of 13 yielded 26 as a mixture of diastereomers. Whereas 22 is inert towards sodium sulfide the higher vinylogs/ethynylogs 23 – 25 furnished the novel thiophene derivatives 28 – 31 . The structures of several ( 22 – 25 , 28 , 29 ) of the new highly unsaturated compounds were determined by single‐crystal X‐ray structural analysis.