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Stereochemistry of the 2 : 1 [4 + 2] adducts of tetrachlorocyclopentadienone acetals with cyclohepta-1,3,5-triene, tropone, cyclohexa-1,4-diene, and p-benzoquinone

Dilys M. Bratby  and  G. I. Fray 

Abstract

The 2 : 1 [4 + 2] adducts of tetrachloropentadienone acetals with cycloheptatriene and cyclohexa-1,4-diene have endo,syn,endo-structures [(III) and (XI)], whereas those with tropone and p-benzoquinone possess endo,anti,endo-geometry [(IV) and (XIII)]. The 2 : 1 adducts derived from cycloheptatriene and cyclohexa-1,4-diene have ‘fixed’ conformations, the central ring systems being sterically incapable of conformational inversion. Variable-temperature n.m.r. studies indicate that conformational rigidity also exists in the 2 : 1 adduct of tropone, although the cyclohept-4-enone ring could in principle undergo a degenerate conformational change [(IVa)⇌(IVb)].

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Article type: Paper
DOI: 10.1039/P19720000195
Citation: J. Chem. Soc., Perkin Trans. 1, 1972,0, 195-199
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    Stereochemistry of the 2 : 1 [4 + 2] adducts of tetrachlorocyclopentadienone acetals with cyclohepta-1,3,5-triene, tropone, cyclohexa-1,4-diene, and p-benzoquinone

    D. M. Bratby and G. I. Fray, J. Chem. Soc., Perkin Trans. 1, 1972, 0, 195
    DOI: 10.1039/P19720000195

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