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ID 46489
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title alternative
Synthesis and Intramolecular Diels-Alder Reaction of 4-Trimethylsiloxy-1, 3, 8-nonatriene
creator
Yamada, Michio
Ohsugi, Masakatsu
Negoro, Kenji
NDC
Chemistry
abstract
Oxy-Cope rearrangement of 4-vinyl-1, .6-heptadien-4-ol [1] at 330°C gave 1, 8-nonadien-4one [4] along with 2, 8-nonadien-4-one [5]. The ketone [4] was converted to the title compound [2] as a mixture of (E)- and (Z)-isomers, by the treatment with LDA and, trimethylsilyl chloride. Alternatively the nonatriene [2] was prepared selectively by the anionic oxy-Cope rearrangement of [1] followed by quenching with trimethylsilyl chloride. Intramolecular Diels-Alder reaction of [2] afforded only cis-3 a-trimethylsiloxy-2, 3, 3 a, 6, 7, 7 a-hexahydro-1 H-indene [3], irrespective of the stereochemistry of [2].
journal title
Journal of the Chemical Society of Japan : chemistry and industrial chemistry
volume
Volume 1987
issue
Issue 2
start page
260
end page
262
date of issued
1987-02-10
publisher
日本化学会
issn
0369-4577
ncid
publisher doi
language
jpn
nii type
Journal Article
HU type
Journal Articles
DCMI type
text
format
application/pdf
text version
publisher
rights
Copyright (c) 1987 The Chemical Society of Japan
relation url
department
Graduate School of Engineering