Organoboron compounds. 370. Allylboron-acetylene condensation by the use of tricrotylborane and the synthesis of 4,6-dimethyl-1-boraadamantane
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Tricrotylborane reacts with propargyl methyl ether with the formation of derivatives of 7-methoxymethyl-8,9-dimethyl-3-borabicyclo[3.3.1]non-6-ene.
The second stage of the allylboron-acetylene condensation — formation of 3-substituted 1,5-diallyl-1-boracyclohex-2-enes — proceeds with the allyl regrouping. Stereospecificity of the second stage of the reaction of tricrotylborane with propargyl methyl ether is observed.
Complexes of 4,6-dimethyl-1-boraadamantane with THF and pyridine are obtained during hydroboronation of 3-methoxy-7-methoxymethyl-8,9-dimethyl-3-borabicyclo[3.3.1]non-6-ene.
On the basis of13C NMR, one methyl group occupies the axial, and the other the equatorial position in 4,6-dimethyl-1-boraadamantane.
KeywordsMethyl Ether Pyridine Allyl Methyl Ether
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