Unexpected formation of highly strained 2,5-Dioxa-3-Silabicyclo[2.1.0]pentane by the reaction of isolable dialkylsilylene with Benzil

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Abstract

The reaction of isolable dialkylsilylene 1 with benzil gave [1+4] cycloadduct 1,3-dioxa-2-sila-cyclopent-4-ene 2 and unexpected 2,5-dioxa-3-silabicyclo[2.1.0]pentane derivative 3. Compound 3 slowly isomerized to 2. The global reaction route mapping method of the model compounds suggests that three reaction paths from an initial silylene-ketone complex (carbonyl silaylide) to 2. A large ring strain energy of model compound for 3 (3) (218.9 kJ·mol-1) was estimated by density functional theory calculations.

Original languageEnglish
Pages (from-to)348-353
Number of pages6
JournalHeteroatom Chemistry
Volume25
Issue number5
DOIs
Publication statusPublished - 2014 Nov 1

ASJC Scopus subject areas

  • Chemistry(all)

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