A series of 1,4-dihalobicyclo[2.2.l]heptanes (2; X = Y = halogens) have been synthesized, characterized, and treated with (trimethylstanny1)lithium (Me,SnLi) in the absence and presence of tert-butylamine (TBA). The product distributions of these reactions have been established by '% and *'%n NMR spectroscopy and vapor-phase

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Comparison of the effect of sp-hybridized carbon on the magnitude of directly bonded and vicinal coupling constants in the labelled nitriles (1)-(7) with that of sp2 and sp3 carbon reveals some interesting, though not major, differences. As noted previously, three-bond coupling involving the labelled carbon and the bridgehead carbon in the bicyclo[n.1.1] alkanes has an important through-space component.

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