Abstract
The transannular reaction of N-benzyl derivatives of 1,11-(methanoaminomethano)-5H,7H-dibenzo[b,g][1,5]selenazocine (1 and 2) with N-bromosuccinimide (NBS) gave an aminoammonio-selenurane 4 which is the first example of an isolable diazaselenurane with two unsymmetrical apical nitrogen ligands of tertiary amino- and quaternary ammonio-groups. X-ray analysis of the aminoammonioselenurane Br− salt (4a) showed the twin-boat form; the distances of Se…N are 1.918 Å and 2.419 Å respectively. The structure of selenurane 4 in solution was confirmed by 77Se and 15N NMR spectroscopy using the 15N-enriched aminoammonio-selenurane 4-15N. The apical tertiary amine of selenurane 4 behaves as a nucleophile toward benzylbromide to give the bisammonio-selenurane 5. The aminoammonio and bisammonio-selenuranes 4 and 5 were converted into the neutral amines upon treatment with 2 equiv. of SmI2.
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