reaction of alkyl phosphites with asymmetric p-quinones khellinquinone and psoralenequinone

ABSTRACT

The reaction of khellinquinone 1 with trialkyl phosphites under varying experimental conditions, has been investigated. In methylene chloride, the reaction of quinone 1 with trimethyl phosphite and triethyl phosphite afforded, mainly, the respective monoalkyl ethers [15 and 16] of khellinquinol 12. The behaviour of psoralenequinone 2 towards attack by dimethyl phosphite and trimethyl phosphite, was also studied. Possible reaction-mechanisms have been considered and structural reasonings were based upon analytical, chemical and spectroscopic grounds