EXPRESSION OF DIPOLAR CHARACTER IN DIYL TRAPPING CHEMISTRY

A set of new reactions is described and illustrated in eqs 1-5. Diazenes which customarily participate in diradical processes, compounds 1a and 9 for example, lead to intermediates which are intercepted by water. Diazene 3 is converted to an intermediate which is intercepted both by water and, when the dielectric constant of the medium is sufficiently high, by n-PrOH. The chemistry is believed to arise through the intermediacy of a "dipolar diradical", which is described by an unequal weighting of the zwitterionic (PSI(alpha) and PSI(beta) and diradical (PSI(delta)) resonance formulations to the overall wave function for the system: PSI = alpha-PSI(alpha) + beta-PSI(beta) + delta-PSI(delta).