AN ARYNE PATHWAY IN DECOMPOSITION OF DIAZOTIZED 2,5-DI-T-BUTYLANILINE

An arynoid adduct 19 can be obtained when 2,5-di-i-butylaniline (16) is diazotized in the presence of furan. In order to decide whether aryne 18 is an intermediate in the decomposition, experiments were undertaken with aniline-d2 as substrate. Mass spectral isotope analyses as well as product yields were used as evidence for possible mechanisms. A partitioning isotope effect was detected, with adduct 19 decreasing in yield with 16-d2 as substrate. Apparent reduction of aryne to arene was observed, particularly in control experiments when furan was omitted as a trap. A consistent reaction scheme including aryne 18 is presented. © 1968, American Chemical Society. All rights reserved.