Tetrahedron p. 7247 - 7262 (1990)
Update date:2022-08-04
Topics:
Glover, Stephen A.
Rowbottom, Colleen A.
Scott, Anthony P.
Schoonraad, Johan L.
Deuterium labelling experiments and n.m.r. studies indicate that cyclisations of N-acyl-N-(2-phenylethyloxy)nitrenium ions occur via direct attack at the ortho position to give 3,4-dihydro-1H-2,1-benzoxazines.In contrast N-acyl-N-(3-phenylpropyloxy)nitrenium ions cyclise to 1,3,4,5-tetrahydro-2,1-benzoxazepines through ipso attack followed by 1,2-carbon migration.In both cases hydrogen circumambulation occurs in the sigma complex before aromatisation.
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