Palladium-catalysed reduction of heteroaromatic naphthyl ethers: Structural effects on reactivity

Experimental conditions for palladium-catalysed hydrogenolysis of tetrazolyl and benzisothiazolyl naphthylmethylic ethers, with a hydrogen donor and with molecular hydrogen, were investigated. Analysis of the structure and reactivity indicates that these compounds are structurally similar to the corresponding benzyloxyderivatives around the ether bond but exhibit different reactivity. It can be concluded from this investigation that 5-chloro-1-phenyltetrazole acts as a better derivatizing agent for naphthyl methanols than 3-chloro-1,2-benzisothiazole-11-dioxide, this contrasting with what has been observed with phenols, allylic and benzylic alcohols.