A New Synthesis of cis-1,6-Diphenyl-2,5,7,10-tetraoxabicyclo[4.4.0]decane and Related Six Membered Cyclic Oxido Compounds

Luigi Lopez; Vincenzo Calò; Francesca Stasi

doi:10.1055/s-1987-28136

Synthesis 1987; 1987(10): 947-948
DOI: 10.1055/s-1987-28136

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A New Synthesis of cis-1,6-Diphenyl-2,5,7,10-tetraoxabicyclo[4.4.0]decane and Related Six Membered Cyclic Oxido Compounds

Luigi Lopez^* , Vincenzo Calò, Francesca Stasi

^*Centro di Studio sulle Metodologie Innovative di Sintesi Organiche, Dipartimento di Chimica, Università di Bari, via Amendola 173, I-70126 Bari, Italy

Abstract

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The synthesis of cis-tetraoxabicyclo decanes 2 and 7 have been performed by treatment of 2,3-diphenyl-5,6-dihydro-1,4-dioxin (1) or cis-2,3,5,6-tetraphenyl-5,6-dihydro-1,4-dioxin (3) with two equivalents of tris (p-bromophenyl)ammonium tetrafluoroborate in a dichloromethane(ethylene glycol mixture. The structural and conformational assignments have been made on the basis of spectroscopical and single crystal X-ray diffraction data. Similar reaction of 2,3,5, 6-tetraphenyl-p-dioxin (4) with the same one electron oxidizing agent in dichloromethane/alcohol mixtures afford trans-2,3-dialkoxy derivatives 8 and 9.

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