Patent ID: 6036892
Filing Date: 2000-03-14
Classification: C07C,C07D,C07F,G01N

Abstract:
A process for preparing a dioxetane salt compound of the formula: ##STR56## having increased storage stability wherein R.sub.3 and R.sub.4 are each selected from the group consisting of acyclic, cyclic and polycyclic organic groups which can optionally be substituted with heteroatoms and which can optionally be joined together to form a cyclic or polycyclic ring group spiro-fused to the dioxetane ring, wherein R.sub.2 is an aryl ring group selected from the group consisting of phenyl and naphthyl groups which can include additional substituents, wherein Z is selected from the group consisting of halogen atoms and alkyl groups of 1-4 carbons, and M is selected from hydrogen, an alkali metal ion or a quaternary ammonium or phosphonium ion comprising the steps of:a) reacting a first alkene compound having the formula: ##STR57## wherein RG is a removable group with a Z-substituted malonate ester and a base to produce a malonate-substituted alkene compound having the formula: ##STR58## wherein R' is an alkyl group of 1-4 carbons; b) photooxygenating the malonate-substituted alkene compound by irradiating a sensitizer in the presence of oxygen and the malonate-substituted alkene compound to form a malonate-substituted dioxetane having the formula: ##STR59## c) reacting the malonate-substituted dioxetane with a phosphorylating reagent having the formula WP(O)Y.sub.2 wherein W and Y are each selected from halogen atoms, substituted or unsubstituted alkoxy, aryloxy, aralkyloxy and trialkylsilyloxy groups to form a phosphorylated dioxetane compound having the formula: ##STR60## d) hydrolyzing the phosphorylated dioxetane in an aqueous solvent with a base of the formula M--Q wherein Q is a basic anion to form the dioxetane salt compound.