Journal of Organometallic Chemistry p. 19 - 28 (1983)
Update date:2022-08-04
Topics:
Mikhailov, B. M.
Gurskii, M. E.
Pershin, D. G.
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.
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Doi:10.1016/S0040-4039(00)81605-6
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