Reaction of methoxyoxirane with inorganic phosphate and reflections on SN2-reactivity

In the context of the chem. of potentially prebiol. natural products it would be important to know whether, from a chem. point of view, glycolaldehyde phosphate could be considered as a potentially prebiol. natural material. In this connection, the reaction of rac. methoxyoxirane with inorg. phosphate in aq. soln. was checked: it does not produce glycolaldehyde phosphate but the 1-phosphate of 1-methoxy-1,2-ethanediol instead. In this context, earlier reflections on the question of how electroneg. substituents influence SN2-reactivity are recorded. [on SciFinder (R)]