REACTIONS OF ASYMMETRICALLY SUBSTITUTED O-QUINONES: 3,5-DI-TERT-BUTYL-1,2-BENZOQUINONE WITH TRIPHENYL-PHOSPHINE, -ARSINE, -STIBINE, THEIR OXIDES AND TRIALKYL PHOSPHATES

Abstract

The entitled quinone 4 reacts with triphenylphosphine (3a) and triphenylarsine (3b) to give the cyclic products 12a and 12b, respectively. The same quinone reacts with triphenylstibine (3c) to yield the stibine-methylene 17. The reaction of oxides of 3a-c (5a-c) and trialkyl phosphates 6a-c with the same quinone 4 affords hydrogen bonded complexes 13a-c and o-quinol monophosphates 23a-c, respectively. In both cases compound 22 is the other product. Possible reaction mechanisms are proposed to explain the formation of the new adducts.

Key Words:

• Asymmetrically o-quinones
• (dioxy)phosphorane
• (dioxy)arsinane
• stibine- methylene
• hydrogen-bonded formulation
• aryl dealkylation