The synthesis of rigid norbornylogs for the purpose of studying orbital interactions through bonds

MN Paddon-Row, E Cotsaris, HK Patney

Index: Paddon-Row, Michael N.; Cotsaris, Evangelo; Patney, Harish K. Tetrahedron, 1986 , vol. 42, # 6 p. 1779 - 1788

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Citation Number: 69

Abstract

2, 3-Dimethylene-7-oxabicyclo [2.2. 1] heptane, available by reduction and dehydration of the furan-fumaroyl chloride Diels-Alder adduct, undergoes ready dibromocyclopropanation at one of its exocyclic double bonds. The corresponding carbenoid, generated by reaction of the dibromide wilh 4 equiv of an organolithium reagent, undergoes the Skattebøl rearrangement to provide a fused cyclopentadiene ring which is immediately ...