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REACTIONS OF BORANES WITH AROMATIC AZIDES. III. A SIMPLE ROUTE TO 1,2-DIHYDRO-N-PHENYL,THIENO- AND THIENO-AZABORINES
Zanirato, Paolo
, p. 285 - 294 (1985)
Some halogeno(organyl)boranes have been formed to promote fragmenatation of organic azides, through decomposition of the Lewis acid-base adducts, to give products whose structure depend on the nature of the reagents.The reactions between α,β-unsaturated ortho-thienylazides and phenylboron dichloride gave 1,2-dihydro-1-phenyl-2-chloro, thieno-, or thieno-azaborines in very good yield, via 1,6-cyclisation of the intermediate N,N-phenyldichloroborylamine resulting from a 1,2-shift of the phenyl group.New 1-phenyl-2-oxybis-(dithieno)-, and -(thieno)--azaborines were prepared by hydrolysis of the labile azaborinechloro derivatives; cyclisation to give these systems involves an intramolecular electrophilic substitution which occurs regiospecificity at the α-position in the thiophene ring.Similar reactions with 2-azidobiphenyl using wider example of chloroboranes, i.e. diphenylboron chloride, phenylboron dichloride, or boron trichloride, led to -2-amine-N-phenyl or carbazole in different ratios (9.0/0.2; 8.0/2.0; 0/10).The results can be interpreted in terms of the degree of concertedness of the three steps of the rearrangement.
