REMOTE INTRAMOLECULAR FUNCTIONALIZATION OF ARYLNITRENIUM IONS: SYNTHESIS OF AMINO-DIHYDROPHENANTHRIDINES AND BENZOCHROMANS.

DOI: 10.1016/S0040-4039(00)83858-7

Source and publish data:

Tetrahedron Letters p. 3705 - 3708 (1986)

Update date:2022-08-03

Topics:

Authors:

Abramovitch, Rudolph A.

Cooper, Melanie M.

Jeyaraman, Ramasubbu

Rusek, Grzegorz

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Article abstract of DOI:10.1016/S0040-4039(00)83858-7

4-Aminobenzochroman (6) and 3-amino-5-acetyl-5,6-dihydrophenanthridine (9) are synthesized by intramolecular trapping of the delocalized nitrenium ions from 3-azidobenzyl phenyl ether and 3-azido-N-benzylacetanilide, respectively.On the other hand, no cyclization product is obtained from 3-azidophenyl benzyl ether, possibly owing to an ortho-effect exerted by the oxygen atom ortho to the developing ?-aryl cation.

Full text of DOI:10.1016/S0040-4039(00)83858-7

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