4-トリメチルシロキシ-1,3,8-ノナトリエンの合成と分子内Diels-Alder反応 <ノート>
日本化学会誌 : 化学と工業化学 Volume 1987 Issue 2
Page 260-262
published_at 1987-02-10
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| File | |
| Title ( jpn ) |
4-トリメチルシロキシ-1,3,8-ノナトリエンの合成と分子内Diels-Alder反応 <ノート>
|
| Title ( eng ) |
Synthesis and Intramolecular Diels-Alder Reaction of 4-Trimethylsiloxy-1, 3, 8-nonatriene
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| Creator |
Yamada Michio
Ohsugi Masakatsu
Negoro Kenji
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| Source Title |
日本化学会誌 : 化学と工業化学
Journal of the Chemical Society of Japan : chemistry and industrial chemistry
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| Volume | 1987 |
| Issue | 2 |
| Start Page | 260 |
| End Page | 262 |
| 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].
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| NDC |
Chemistry [ 430 ]
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| Language |
jpn
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| Resource Type | journal article |
| Publisher |
日本化学会
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| Date of Issued | 1987-02-10 |
| Rights |
Copyright (c) 1987 The Chemical Society of Japan
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| Publish Type | Version of Record |
| Access Rights | open access |
| Source Identifier |
[ISSN] 0369-4577
[NCID] AN00186595
[DOI] 10.1246/nikkashi.1987.260
[DOI] https://doi.org/10.1246/nikkashi.1987.260
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