Synthesis and ¹³C N.M.R. Studies of Some Polycyclic Hydrocarbons with Trimethyltin at the Bridgehead

Abstract

The synthesis of (adamantan-1-yl)trimethylstannane (1), (bicyclo[2,2,2]oct-1-yl)trimethylstannane (2), (bicyclo[2,2,1]hept-1-yl)trimethylstannane (3), (cubanyl)trimethylstannane(4) and tricyco[[4,1,1,0^2,7]- hept-1-yl)trimethylstannane (5) is described and the carbon-13 nuclear magnetic resonance spectra of these compounds are reported. In particular, it is found that the coupling constant of the directly bonded tin bridgehead carbon atoms is not greatly dependent on the degree of s character of the carbon exocyclic bonding orbital and that vicinal coupling between tin and carbon is observed to fit a Karplus equation. A linear relationship occurs between ¹J(^117,119Sn,¹³C_Me) and ²J(^117,119Sn,¹³H_Me).