ORGANOBORON COMPOUNDS. CDIII. IODINATION OF ATE COMPLEXES OF 1-BORAADAMANTANE

Article abstract of DOI:10.1016/S0022-328X(00)98647-9

The complex of 1-boraadamantane with tetrahydrofuran (1) reacts with iodine in the presence of lithium methylate or methyllithium to produce 3-methoxy- (III) and 3-methyl-7-iodomethyl-3-borabicyclo<3.3.1>nonane (X), respectively.Further iodination of III in the presence of lithium methylate proceeds in a complicated manner due to replacement of iodine by the methoxy group in the starting compound.The high reactivity of the halogen in III permitted a one-pot synthesis of 3-methoxy-7-methoxymethyl-3-borabicyclo<3.3.1>nonane from I.Iodination of lithium 1-isopropenyl-1-boraadamantanate leads, after methanolysis, to 3-methoxy-7-isobutenyl-3-borabicyclo<3.3.1>nonane.The latter compound was converted to 7-isobutenyl-3-methyl-3-borabicyclo<3.3.1>nonane on treatment with MeMgI.