The Journal of Organic Chemistry

Formation of homologous bird-cage molecules. Strain and transannular effects

DC Dong, JT Edward

Index: Dong, Dao Cong; Edward, John T. Journal of Organic Chemistry, 1980 , vol. 45, # 12 p. 2395 - 2399

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Citation Number: 9

Abstract

Results Synthesis of Cage Compounds 4 and 5. The insecticide “Isodrin”(3, n= 1) is made by'the Diels-Alder reaction of cyclopentadiene (2, n= 1) with hexachloronorbornadiene (1); 2b homoisodrin (3, n= 2) and bishomoisodrin (3, n= 3) were prepared in good yields by similar reactions of 1, 3-cyclohexadiene (2, n= 2) and 1, 3-cycloheptadiene (2, 71= 3). Ultraviolet irradiation of the Isodrin homologues in acetone3i6 gave the hexachloro cage