Synthesis of stable water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Claim 1

A compound having the formula: ##STR86## wherein R 1 is a trialkylsilyl group or a lower alkyl group having up to 12 carbon atoms; R 2 is meta or non-conjugated with the ring carbon atom of the Y group where the phosphonate ester containing side chain is attached, and is a hydroxyl group, an ether (OR 4 ) or a thioether (SR 4 ) group wherein R 4 is a substituted or unsubstituted alkenyl, lower alkyl or aralkyl group having up to 20 carbon atoms, an acyloxy group, a bromine atom, an amino group, a mono or di(lower) alkylamino group or its acid salt wherein each lower alkyl group has up to 7 carbon atoms and wherein each lower alkyl group may be bonded to the Y group forming one or more fused rings, a NHSO 2 R 5 group wherein R 5 is a methyl, tolyl, or trifluoro group, a substituted aryl, heteroaryl, or β-styrenyl having up to 20 carbon atoms; R 3 is a substituted or unsubstituted lower alkyl, aralyl or heteroaralkyl group having up to 20 carbon atoms, an aryl or heteroaryl group having up to 14 carbon atoms which can be further substituted; X 1 is hydrogen or a substituted or unsubstituted aryl, aralkyl, heteroaryl, or a heteroalkyl group having up to 20 carbon atoms, an allyl group, a hydroxy (lower) alkyl group having up to 6 carbon atoms, a (lower) alkyl-OSiX 3 group wherein the alkyl and X radicals are as defined above, an ether (OR 4 ) or a thioether (SR 4 ) wherein R 4 is as defined above, an SO 2 R 6 group wherein R 6 is methyl, phenyl or NHC 6 H 5 , a substituted or unsubstituted alkyl group having up to 7 carbon atoms, a nitro group, a CN group, an aldehyde or its oxime or dimethyl hydrazone, a haologen group, a carboxylic acid salt, ester, or hydrazide, a trialkyl silicon-based group, or a phosphoryloxy group; and Y is phenyl, biphenyl, 9,10-dihydrophenanthryl, naphthyl, anthryl, phenanthryl, pyrenyl, dibenzosuberyl, phthalyl or derivatives thereof.