A supramolecular protecting group strategy introduced to the organic solid state: Enhanced reactivity through molecular pedal motion

Elizabeth Elacqua, Poonam Kaushik, Ryan H. Groeneman, Joseph C. Sumrak, Dejan Krešimir Bučar, Leonard R. MacGillivray

Research output: Contribution to journalArticlepeer-review

78 Scopus citations

Abstract

A supramolecular protecting group strategy has been applied to achieve solid-state photodimerizations of olefins lined with a combination of hydrogen-bond-donor and -acceptor groups. Esters were used as protecting groups to generate head-to-head photodimers that were readily converted into diacids. A protected olefin equipped with a stilbene unit exhibits enhanced reactivity that is ascribed to pedal motions in the solid state (orange hexagons: template: blur circles: recognition sites).

Original languageEnglish (US)
Pages (from-to)1037-1041
Number of pages5
JournalAngewandte Chemie - International Edition
Volume51
Issue number4
DOIs
StatePublished - Jan 23 2012

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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