• Applied Biological Chemistry
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• v.39 no.3
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• pp.227-234
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• 1996

4-Methyl-2,6,7-trioxa-1-phosphabicyclo [2,2,2] octane 1-sulfide (BPS), 4-Methyl-2,6,7-trioxa-1-phosphabicyclo[2,2,2] octane 1-oxide (BPO) and related monocyclic methylphosphates were prepared and the oxidation of BPS with MCPBA in chlorofrom or methanol was carried out to investigate the formation of reactive intermediates and reaction mechanism. BPO was the only product in chloroform while in methanol isomeric monocyclic methylphosphates were formed through opening of bicylic structure with subsequent phosphorylation of methanol by reactive intermediate formed in reaction. Formation of little amount of BPO was also observed. The structure of phosphorylating intermediate was probed with various spectroscopic methods and monocyclic methyl sulfenyl ester was suggested as a possible structure.