Abstract
1,3-Dipolar reagents with an unsaturated CNO- or CNN-skeleton undergo 1,3-organoboration by triorganoboranes. On the other hand, the unsaturated NNO-skeletons in azoxybenzene or nitrous-oxide are reduced to the corresponding NN-fragment by trialkylboranes. The 1,3-addition of aminoborane Cl2BNMe2 to the aldimineoxide PhHC = NMe-0 represents one of the rare examples of analogous reactivity of BN- and CC-double bonds. O-Borylhydroxylamines PhHCR-NMe-OBR2 are reduced by BR′3 to PhHCR-NMe-BR′2 and R′0-BR2. Similar reduction products are isolated from liquid-phase thermolysis of PhHCEt-NMe-OBEt2 (16), whereas gas-phase thermolysis of 16 gives PhCH = NMe, (EtBO)3, and C4H10.

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