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Paper | Special issue | Vol 47, No. 1, 1998, pp.283-288
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)14
Synthesis of Polycyclic 1,2-Dioxanes from Endoperoxides

Charles W. Jefford,* Harald Eschenhof, and Gérald Bernardinelli

*Department of Organic Chemistry, Laboratory fo Crystallography, University of Geneva, 30, quai Ernest Ansermet, 1211 Geneva 4, Switzerland

Abstract

1,4-Diphenylcyclohex-2-ene 1,4-endoperoxide (7) on catalysis with trimethylsilyl trifluoromethanesulfonate (TMSOTf) in CH2Cl2 at -78°C reacted partially with 1,4-diphenylcyclopenta-1,3-diene (5) to give 3a,5a,6,7,9a,9b-hexahydro-2,5a,8,9b-tetraphenyl-1H-4,5-dioxacyclopenta[a]naphthalene (8) in 7.5% yield. Similar reaction of 1-phenylcyclohex-2-ene 1,4-endoperoxide (9) with1-phenylcyclohexa-1,3-diene (10) afforded three 1,2-dioxanes in a combined yield of 45%, one of which was identified as 1,2,4a,6a,7,8,10a,10b-octahydro-3,9-diphenyl-5,6-dioxaphenanthrene (11). The TMSOTf-catalysed reaction of 1,4-dihydro-1,4-dimethylnaphthalene 1,4-endoperoxide (12) with 1,4-diphenyl-cyclopenta-1,3-diene (5), benzofuran (14) and 1,1-diphenylethylene (16) gave the endo cis-fused tricyclic 1,2-dioxanes, (13), (15), and the cis-fused bicyclic 1,2- dioxane (17) as single products in yields of 46, 81, and 72% respectively. The structures of 8, 11, 13, 15 and 17 were elucidated by X-Ray analysis.