The dissociative route in the alkaline hydrolysis of aryl 4-hydroxy-β-styrenesulfonates

被引:8
作者
Cevasco, G [1 ]
Thea, S [1 ]
机构
[1] CNR, Ctr Studio Chim Composti Cicloalifat & Aromat, Dipartimento Chim & Chim Ind, Ist Nazl Coordinamento Chim Sistemi Biol, I-16146 Genoa, Italy
关键词
D O I
10.1021/jo971508w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactivity comparisons, activation parameters, and the substituent effect in the leaving group indicate that the hydrolysis of title esters in moderately to strongly alkaline aqueous solution follows a dissociative pathway with the probable participation of an extended sulfoquinone (thioquinone dioxide) intermediate. The interposition of a vinylene group between the internal nucleophile and the reaction site favors the elimination-addition process. Present results further suggest the high tendency of suitably substituted sulfonyl derivatives to hydrolyze through dissociative mechanism.
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页码:2125 / 2129
页数:5
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