98569-91-6Relevant articles and documents
Gas-phase Rearrangement and Cyclisation Reactions of 2-Benzylphenylaminyl Radicals and Related 2-Hetero-analogues
Cadogan, J. I. G.,Hickson, Clare L.,Hutchison, H. Susan,McNab, Hamish
, p. 377 - 384 (2007/10/02)
Gas-phase pyrolysis of the appropriate N-allyl or N-benzyl compound leads to the aminyl radicals 1 (X = NH, Y = CH2, CO, S, or O).Equilibration of these via the spirodienyl 2 gives mixtures of isomeric acridans or acridones as major products from radicals 1 (X = NH, Y = CH2 and Y = CO, respectively) and isomeric phenothiazines as minor products from radical 1 (X = NH, Y = S).The major product in this case is the aminodibenzofuran 29 which may be formed by H-abstraction by the aminyl to give an aryl radical, followed by cyclisation (Scheme 6).The only cyclised product from radical 1 (X = NH, Y = O) is the carbazole 35, formed by a mechanism similar to that of Scheme 6, but in which H-abstraction by the rearranged phenoxyl radical has taken place.
