Jac. Alves et al., METAL-ASSISTED REACTIONS .26. CATALYTIC REACTIVITY AND ETHER BOND LENGTHS IN ARYLOXYTETRAZOLES AND ARYLOXYPSEUDOSACCHARINS, Perkin transactions. 2, (4), 1997, pp. 669-677
X-Ray structure determinations on a variety of aryloxytetrazoles 1 and
aryloxypseudosaccharins 4 have shown that the central C-O-C ether lin
kage is remarkable in having one very long C-O bond and one very short
one. The central C-O-C bond angle is close to 120 degrees. The implic
ations of these effects on the reactivity of compounds 1 and 4 towards
catalytic hydrogenolysis or cross-coupling are explored.