Dichlorination of (hexadehydro-diels-alder generated) benzynes and a protocol for interrogating the kinetic order of bimolecular aryne trapping reactions

Dawen Niu, Tao Wang, Brian P. Woods, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

36 Scopus citations

Abstract

The efficient dichlorination of benzynes prepared by the hexadehydro-Diels-Alder (HDDA) reaction is reported. Cycloisomerization of a triyne substrate in the presence of dilithium tetrachlorocuprate is shown to provide dichlorinated products A by capture of the benzyne intermediate. A general strategy for discerning the kinetic order of an external aryne trapping agent is presented. It merely requires measurement of the competition between bimolecular vs unimolecular trapping events (here, dichlorination vs intramolecular Diels-Alder (IMDA) reaction to give A vs B, respectively) as a function of the concentration of the trapping agent.

Original languageEnglish (US)
Pages (from-to)254-257
Number of pages4
JournalOrganic Letters
Volume16
Issue number1
DOIs
StatePublished - Jan 3 2014

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