Catalytic epoxidation of 5-vinyl-2-norbornene with organic hydroperoxides

被引:0
|
作者
Osokin, MY [1 ]
Karpov, OP
Kryukov, SI
Surovtsev, AA
Osokin, YG
Bychkov, BN
机构
[1] Yaroslavl State Tech Univ, Yaroslavl, Russia
[2] OAO Yarsintez Res Inst, Yaroslavl, Russia
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中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
5-Vinyl-2-norbornene is epoxidized with tert-butyl, tert-amyl, or cumyl hydroperoxide in the presence of molybdenyl ethanediolate at either or both of the double bonds of the hydrocarbon to afford preferentially 2,3-epoxy-5-vinylnorbornane. The reactivity of tert-alkyl hydroperoxides correlates with their structure characterized by the Taft polar substituent constants. The rho* value found to be 1.08 confirms the electrophilic character of the catalytic hydroperoxide epoxidation and indicates a low polarity of the activated complex of the reaction.
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页码:410 / 414
页数:5
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