Dioxopyrrolines.XLII. : Mechanism of 7-Epimerization Reaction of 7-Substituted 5-Ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones
この論文をさがす
説明
7-Mono- and 7,7-disubstituted 5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones undergo epimerization at C-7 when treated when treated with base. Experiments using the stereospecifically deuterium labeled compound 6 showed that the inversion of stereochemistries at C-6 and C-7 took place simutaneously in this reaction, thus proving that the reaction proceeded through C_1-C_5 bond fission and recyclization. The suggested intermediate 10 with a highly strained seven membered ring would give either the C_7 epimerized product by a fast recombination or irreversibly give the dihydroazatropolones 9 by a trans- to cis- isomerization of the C=N double bond. Kinetic treatments showed that the latter reaction is slower than the former equilibrium reaction.The analogous 7-epimerization reaction observed in the hydride reduction of the 4-oxo group and in the photolysis of the imidate 24 was proved to proceed with a similar mechanism.
収録刊行物
-
- Chemical & pharmaceutical bulletin
-
Chemical & pharmaceutical bulletin 37 (3), 652-659, 1989-03-25
公益社団法人日本薬学会
- Tweet
キーワード
詳細情報 詳細情報について
-
- CRID
- 1571417127438553856
-
- NII論文ID
- 110003627579
-
- NII書誌ID
- AA00602100
-
- ISSN
- 00092363
-
- 本文言語コード
- en
-
- データソース種別
-
- CiNii Articles