Nicodem (Hive Bee) 07-16-04 07:25 No 519757				Methylating with a pesticide?
						OK, I know this question seams crazy, but did anybody considered (or tried) using a pesticide called “dichlorvos” as a methylation reagent? Dichlorvos structure: (MeO)2PO-O-CH=CCl2      http://www.alanwood.net/pesticides/dichlorvos.html Synonyms: http://www.cdc.gov/niosh/rtecs/tc55730.html#L Toxicology and other info: http://www.inchem.org/documents/pds/pds/pest2_e.htm One of the preparations (NogosTM) is a 50% solution in xylene which is just perfect. Yeah, I know it’s a pesticide but it would still be much safer than dimethyl sulphate since it is not that toxic to humans. Trimethyl phosphate seams to work satisfactorily as a methylation reagent so I see only few reasons why this dimethyl dichlorovinyl phosphate would not. One problem I see is that it would probably not work with plain phenols like p-MeO-phenol since there is danger of its condensation with the reactive dichloroacetaldehyde which would form from the reagent degradation. But I think it might work with hydroxy benzaldehydes like syringaldehyde, 2-hydroxy-5-MeO-benzaldehyde and similar, ring enough deactivated, compounds. The other problem is that the dichlorovinyl group might bee the first to hydrolyze, leaving the much less or non effective (MeO)2HPO2. Maybe it would nevertheless work if used in the melt phase like in ../rhodium /me3po4.html though I'm concerned it might form O-blocked phenols of the type Ar-O-CH=CCl2 in the absence of water. But if the dichlorovinyl group is truly the best leaving group it should bee possible to solvatize/transesterify dichlorvos in refluxing methanol yielding (MeO)3PO and Cl2C-CH(OMe)2. Maybe this mixture could bee used directly as a methylenation agent without even separating the dichloroacetaldehyde dimethylacetal out? Sorry if somebee finds this stupid. I’m just playing with the thought of a “ready to use” OTC methylation reagent. “The real drug-problem is that we need more and better drugs.” – J. Ott