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A Comparison of Carbon-Carbon Double Bond and Cyclopropane as Neighboring Groups. Solvolysis Rates of 1-Aryl-4-cyclopropylbutyl Chlorides

D. Ostović ; Faculty of Pharmacy and. Biochemistry, University of Zagreb, Kovaciceva 1, 41000 Zagreb, Yugoslavia
O. Kronja ; Faculty of Pharmacy and. Biochemistry, University of Zagreb, Kovaciceva 1, 41000 Zagreb, Yugoslavia
S. Borčić ; Faculty of Pharmacy and. Biochemistry, University of Zagreb, Kovaciceva 1, 41000 Zagreb, Yugoslavia

Sažetak

1-Phenyl-4-cyclopropylbutyl chloride 13a and 1-m-bromophenyl-
4-cyclopropylbutyl chloride 13b were prepared and their
solvolysis rates measured. As with corresponding 1-aryl-5-hexenyl
chlorides 9, no reaction rate increases were observed. In contrast,
1-aryl-5-methyl-5-hexenyl chlorides 10 and 1-aryl-5-heptenyl chlorides
11 which are isomeric to 13 solvolyze with significant anchimeric
assistance of the methyl-substituted aliphatic double bond.
This failure of the cyclopropane ring to act as a neighboring group
is rationalized in terms of possible charge delocalization in the
reaction transition state arising from 13 and from 10 or 11.

Ključne riječi

Hrčak ID:

194337

URI

https://hrcak.srce.hr/194337

Datum izdavanja:

20.7.1981.

Posjeta: 657 *