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6-Exo-dig and/or 7-endo-dig iodocyclization reactions of functionalized acetylenic derivatives with ICl are disfavored in comparison with the corresponding electrophilic addition reactions providing regioselectively (E)-1-chloro-2-iodoethene derivatives. On the contrary, 6-endo-digand 5-exo-dig iodocyclizations of methyl ynoates with ICl seem to be favored in comparison with the corresponding electrophilic addition reactions.
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Bellina et al. (2003) studied this question.
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