Reaction of 2,3-Dihydro-1H-1,3,2-diazaboroles and Diphenylketene: A Novel Synthesis of 1,3,2-Oxazaborolidines.
Reaction of equimolar amts. of diphenylketene with 1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaboroles [shown as I; X = Br (1a), F (1b), NH2 (1c), NMe2 (1d), Me (1e), SnMe3 (1f), CH:C(SnMe3)C6H4Cl-4 (1g)] regioselectively afforded good yields of the corresponding 1,3,2-oxazaborolidines (shown as II; same X; 2a-g). The x-ray structure anal. of 2d revealed an essentially planar five-membered heterocycle with a long B-O bond and a strong exocyclic BN-p bond.
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