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- W1550078494 abstract "The stereochemistry of the reaction of cis- and trans-stilbene-2-carboxylic acids with chlorine and bromine, yielding the two diastereoisomeric 3-phenyl-4-halo-3:4-dihydroisocoumarins (III) and (IV) has been investigated. The reactions are entirely stereospecific and involve intramolecular attack by the carboxyl group on an intermediate carbonium or halonium ion. The lactones (III) and (IV) yield the two 3-(α-hydroxybenzyl) phthalides (V) and (VI), with retention of configuration. Thionyl chloride transforms (V) and (VI) into the 3-(α-chlorobenzyl) phthalides (IX) and (X), with inversion. Steric effects are mainly responsible for the alternative formation of halolactones or normal dihalogenated derivatives in the reactions between unsaturated acids and halogens." @default.
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- W1550078494 date "1958-01-01" @default.
- W1550078494 modified "2023-10-13" @default.
- W1550078494 title "Stereochemistry of the halolactonisation reaction" @default.
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- W1550078494 doi "https://doi.org/10.1016/0040-4020(58)80060-5" @default.
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