Synthesis of mercaptaryl or hydroxyaryl enol ether alkali metal salts

A process for preparing a hydroxyaryl enol ether alkali metal salt having the formula:

• ##STR14## in which T is a substituted or unsubstituted adamant-2-ylidene group, OR.sup.3 is an ether group, Y is a light-emitting fluorophore-forming group which will be part of a luminescent substance formed by decomposition of a 1,2-dioxetane subsequently formed from the hydroxyaryl enol ether alkali metal salt, capable of absorbing energy to form an excited state from which it emits optically detectable energy to return to its ground state, and AM.sup.+ is an alkali metal cation, which comprises the step of carrying out ester cleavage with an alkali metal alkoxide in a lower alkanol on an esterified aryl enol ether having the formula:
• ##STR15## in which R.sup.4 is a pivaloyl group, under anhydrous conditions to give the hydroxyaryl enol ether alkali metal salt.

A process for preparing a hydroxyaryl enol ether lithio salt having the formula:

• ##STR16## in which T is a fused, substituted or unsubstituted polycycloalkylidene group, OR.sup.3 is an ether group, and Y is a light-emitting fluorophore-forming group which will be part of a luminescent substance formed by decomposition of a 1,2-dioxetane subsequently formed from the hydroxyaryl enol ether alkali metal salt, capable of absorbing energy to form an excited state from which it emits optically detectable energy to return to its ground state, which comprises (1) reacting a corresponding dialkyl 1-alkoxy-1-arylmethane phosphonate having the formula:
• ##STR17## in which R.sub.1 is an alkyl group and R.sub.2 is a hydroxy protecting acyl group that will be substantially cleaved during the reaction, with three equivalents of a lithium alkyl compound in solution at low temperature under an inert atmosphere, and (2) adding to the resulting mixture containing the corresponding phosphonate-stabilized .alpha.-carbanion a ketone having the formula T=O and reacting to give the hydroxyaryl enol ether lithio salt.