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Die Solvolyse von α-Bromstyrolen Substitution am ungesättigten trigonalen Kohlenstoffatom (1964)

Grob, C. A. ; Cseh, G.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 47 (1964), S. 194-203

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ISSN: 0018-019X

Keywords: Chemistry ; Organic Chemistry

Source: Wiley InterScience Backfile Collection 1832-2000

Topics: Chemistry and Pharmacology

Notes: In ‘80%’ ethanol the or-bromostyrenes 5a-5d undergo unimolecular solvolysis to the corresponding acetophenones. In addition to acetophenone, α-bromostyrene itself yields a minor amount of phenylacetylene. The p-amino, p-methoxy and p- acetamido derivatives 5b-5c react 108, 104 and 103 times as fast, respectively, as the unsubstituted compound 5a, the rates being insensitive to 1-5 equivalents of triethyl- amine. Furthermore, 5a and 5c show electrophilic catalysis by silver ion. A two-step ionisation mechanism involving a digonal carbonium ion (p-R-C6H4C=CH2)+ is thus indicated.

Type of Medium: Electronic Resource

URL: http://dx.doi.org/10.1002/hlca.19640470126

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