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- W2000458609 abstract "A kinetic study has been made of the cycliacylation in liquid HF of protonated 3-phenylpropanoic and 4-phenylbutanoic acids and a number of their alkyl derivatives to the corresponding 1-indanones and 1-tetralones*. The acylating species in these reactions has been shown to be the free acyl cation. Formation of this cation becomes rate-determining at high rates of the cyclization step proper and then masks any further activation of the benzene ring. The cyclization to 1-indanones, but not that to 1-tetralones, exhibits an unusually large ortho partial rate factor (for methyl groups fo is as large as fp). PMR spectroscopic data indicate that replacement of the benzylic hydrogen atoms in 3-phenylpropanoic acids by methyl groups has a great influence on the conformation around the C(2)-C(3) bond. This results in a proximity effect that accelerates the cyclization reaction by a factor of about 102." @default.
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- W2000458609 date "2010-09-02" @default.
- W2000458609 modified "2023-09-25" @default.
- W2000458609 title "Cycliacylation of 3-phenylpropanoic and 4-phenylbutanoic acids in liquid hydrogen fluoride: Kinetics, mechanism and substituent effects" @default.
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- W2000458609 doi "https://doi.org/10.1002/recl.19740930705" @default.
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