Intramolecular ring closure via ether bond in reaction of α,α′ halogeno bicyclo[3.3.1]nonanediones under basic conditions

被引:9
作者
Butkus, E [1 ]
Kubilius, R [1 ]
Stoncius, S [1 ]
Zilinskas, A [1 ]
机构
[1] Vilnius State Univ, Dept Organ Chem, LT-2734 Vilnius, Lithuania
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 11期
关键词
D O I
10.1039/a901620a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The stereoselectivity of halogenation of bicyclo[3.3.1]nonan-2-one 1 and bicyclo[3.3.1]nonane-2,6-dione 2 with molecular bromine and chlorine was studied. The transformation of alpha-bromo- and chloro-bicyclo[3.3.1]nonanones 3-5 under Favorskii reaction conditions was studied. The reaction of alpha,alpha'-dihalogeno diones in the presence of sodium methoxide, ethoxide, propoxide and potassium cyanide led to the intramolecular ring closure via C-O bond formation giving the highly functionalized chiral 2-oxatricyclo[4.3.1.0(3,8)]decane (2-oxaprotoadamantane) structure. Enantiomers of this cage structure were resolved by chiral GLC. The intramolecular ring closure pathway involving the intermediate alkoxybicyclo[3.3.1]nonanolate structure was proposed.
引用
收藏
页码:1431 / 1436
页数:6
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