Journal of the Chemical Society. Perkin transactions I p. 565 - 573 (1981)
Update date:2022-09-26
Topics: Intramolecular Cycloaddition
Bishop, Roger
Parker, William
Stevenson, James Ronald
Reactions likely to involve C(2)-C(6) and C(2)-C(7) intramolecular reactions in bicyclo<3.3.1>nonane derivatives are discussed in terms of the conformations available to the ring system.While endo-6-hydroxybicyclo<3.3.1>nonan-2-one (11) incorporated three deuterium atoms (excluding the hydroxy-group) on heating with NaOD, the exo-isomer (17) exchanged the six hydrogens adjacent to the oxygenation functions but not the carbinyl proton.Evidence is presented favouring a stereospecific base-induced 2,6-hydride migration, most probably proceeding via a twin-twist boat transition state.Treatment of 6,6-ethylenedioxy-2-methoxymethylenebicyclo<3.3.1>nonane (36) with aqueous HCl in acetone produced 2-hydroxyprotoadamantan-10-one (38) in high yield.This process resulted from hydrolysis of the oxygenated groups thereby liberating the endo-keto-aldehyde intermediate (37) which underwent subsequent intramolecular aldol condensation between the C(2) aldehyde and C(7).
View MoreTaimai Sanluck Pharmaceutical Co.,Ltd
Contact:86-592-7662921
Address:8D,No.186,Huarong Road,Huli,Xiamen,China
Huangshan Honghui Pharm Technology Co., Ltd.(expird)
website:http://www.honghuichem.com
Contact:18855958372
Address:Qingshan Wan No.1,Nanyuan Kou,SheXian Huangshan City,Anhui Province
Longhui qunfeng Chemical Co., Ltd
Contact:86-731-82173407
Address:South-east Industrial Park, Longhui County, Hunan Province, China
Tianjin Tensing Fine Chemical Research Develop Centre
Contact:86-022-23718576,13032267585
Address:2-2-201,13 Guiyuan road,Huayuan Industry district,Tianjin,china
KINHENG CHEMICAL(SHANGHAI)CO., LTD.
Contact:+8621-60490170
Address:Room401, No.28,Lane 189, Yangshupu Rd. Shanghai, China.
Doi:10.1021/om049574t
(2004)Doi:10.1021/ic040006f
(2004)Doi:10.1039/P19900001091
(1990)Doi:10.1071/CH9651273
(1965)Doi:10.1246/bcsj.43.3013
(1970)Doi:10.1134/S0036024418040106
()
