"When the halogenation reaction is carried out on a cycloalkene, such as cyclopentene, only the trans stereoisomer of the dihalide addition product is formed rather than the mixture of cis and trans isomers that might have been expected if a planar carbocation intermediate were involved. We say that the reaction occurs with anti stereochemistry ..."
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John McMurry, Organic Chemistry 8th ed. (2012), Ch. 8 : Alkenes: Reactions and Synthesis.
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Halogenation
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