ORGANOBORON COMPOUNDS. CDXIV. HOMOLOGATION OF 3-METHOXY-7-METHYL-3-BORABICYCLONONANE AND 3-METHOXY-7-METHOXYMETHYL-3-BORABICYCLONON-6-ENE USING α-HALOALKYLLITHIUM COMPOUNDS. SYNTHESIS OF 3-BORABICYCLODECANE AND 3-BORABICYCLODEC-7(8)-ENE DERIVATIVES

Article abstract of DOI:10.1016/0022-328X(84)80329-0

3-Methoxy-7-methyl-3-borabicyclo<3.3.1>nonane (I) and 3-methoxy-7-methoxymethyl-3-borabicyclo<3.3.1>non-6-ene (X) react with α-halomethyllithium compounds at <= -110 deg C to yield 3-methoxy-8-methyl-3-borabicyclo<4.3.1>decane and a mixture of 3-methoxy-8-methoxymethyl-3-borabicyclo<4.3.1>dec-7-ene and 3-methoxy-8-methoxymethyl-3-borabicyclo<4.3.1>dec-8-ene.A similar reaction of I or X with α-bromomethyllithium leads to the corresponding endo-4- and exo-4-methyl derivatives of 3-borabicyclo<4.3.1>decane and 3-borabicyclo<4.3.1>dec-7(8)-ene.