Abstract
The preparation of trans-1,2-bis(triphenylphosphonio)benzocyclobutene dibromide and its conversion to 1,2-bis(triphenylphosphoranyl)benzocyclobutene are described. Treatment of the dibromide salt with base followed by reaction with a benzaldehyde affords different results that depend upon the nature of the solvent. In ethanol as the major solvent, the principal products are the cis- and trans-1-benzylidenebenzocyclobutenes corresponding to the particular benzaldehyde used, together with triphenylphosphine oxide; in DMF or DMSO, the major products are the cis,cis- and/or cis,trans- and/or trans,trans-1,2-bisbenzylidenebenzocyclobutenes corresponding to the benzaldehydes used, as well as triphenylphosphine oxide. In both instances a number of minor products are obtained. The structure and stereochemistry of the major products are in accord with the chemical and physical data reported herein.
Original language | English (US) |
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Pages (from-to) | 4996-5007 |
Number of pages | 12 |
Journal | Journal of the American Chemical Society |
Volume | 89 |
Issue number | 19 |
DOIs | |
State | Published - Sep 1 1967 |
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry