The chemistry of substituted norbornenes. Reactions of 5-vinyl-2-norbornene and 5-ethylidene-2-norbornene with formic acid.
-
- Inoue Yoshiharu
- Research Institute for Production Development, 15
-
- Tanimoto Fumio
- Research Institute for Production Development, 15
-
- Kitano Hisao
- Research Institute for Production Development, 15
説明
Addition of formic acid to 5-vinyl-2-norbornene(1) and subsequent hydrolysis afford 6-vinyl-exo-2-norbornanol(5) and 5-vinyl-exo-2-norbornanol(6). Similarly, from 5-ethylidene-2-norbornene(2) are formed 6-ethylidene-exo-2-norbornanol(14), 5-ethylidene-exo-2-norbornanol(15), and 6-ethyltricyclo[2.2.1.02,6]heptan-3-ol(16). The hydroboration of 2 also leads to the formation of 14 and 15. Thus, the vinyl- and ethylidene-exo-norbornanols, 5, 6, 14, and 15, and the corresponding endo-norbornanols, 9, 10, 21, and 22, have been synthesized. A structural analysis of these products by 13C NMR revealed that under certain conditions, the ethylidene group of 2 exerts a great influence upon the reactivity of the norbornenyl ring double bond. Moreover, the fact that 16 derived from the addition of formic acid to 2 consists of both exo- and endo-hydroxy epimers is inconsistent with the previous observations that the exo-isomer is generally the sole product in related systems.
収録刊行物
-
- Bulletin of the Chemical Society of Japan
-
Bulletin of the Chemical Society of Japan 57 (9), 2468-2473, 1984
公益社団法人 日本化学会
- Tweet
キーワード
詳細情報 詳細情報について
-
- CRID
- 1390001204124419456
-
- NII論文ID
- 130001984154
-
- ISSN
- 13480634
- 00092673
-
- 本文言語コード
- en
-
- データソース種別
-
- JaLC
- Crossref
- CiNii Articles
- OpenAIRE
-
- 抄録ライセンスフラグ
- 使用不可
