Sometimes you come across a bond in chemistry that just shouts at you. This happened to me in 1989[cite]10.1039/C39890001722[/cite] with the molecule shown below. Here is its story and, 26 years later, how I responded.
Posts Tagged ‘New Hampshire’
Fine-tuning a (hydrogen) bond into symmetry.
Friday, January 23rd, 2015Why diphenyl peroxide does not exist.
Monday, April 29th, 2013A few posts back, I explored the “benzidine rearrangement” of diphenyl hydrazine. This reaction requires diprotonation to proceed readily, but we then discovered that replacing one NH by an O as in N,O-diphenyl hydroxylamine required only monoprotonation to undergo an equivalent facile rearrangement. So replacing both NHs by O to form diphenyl peroxide (Ph-O-O-Ph) completes this homologous series. I had speculated that PhNHOPh might exist if all traces of catalytic acid were removed, but could the same be done to PhOOPh? Not if it continues the trend and requires no prior protonation at all!