Phenyldiazomethane synthesis

Creary, X. Tosylhydrazone salt pyrolyses Phenyldiazomethanes. Diazomethane synthesis. Org. Syn. 1986, 64, 207-216. 

The diazirino-mannose derivative 80 has been synthesized from the corresponding mannonolactone oxime (i, MsCl ii, NH3. MeOH iii, I2, EtjO). The use of this and other diazirino-sugars in die synthesis of O- and C-glycosides is covered in Chapter 3. oc-D-Glucopyranosyl-phenyldiazomethane 81 has been synthesized as a mechanism-based a-glucosidase inhibitor. ... 

Huisgen s group have also investigated the possibility that 1,3-dipolar cycloadditions could proceed via three-membered-ring intermediates, (74) -> (75). They have investigated this mechanism by synthesis of the possible intermediates (74) in the reactions between styrene and benzo-nitrile-4-nitrobenzylide (76), phenyldiazomethane, and 4-nitrophenyl azide. 

Other Alkyl and Aryl Ethers. - The reagent system of allyl ethyl carbonate and a Pd(0) catalyst, applied to carbohydrate alcohols, has been utilised for making allyl ethers under neutral conditions. The synthesis of benzyl ethers from the parent alcohols under non-basic conditions has been achieved using phenyldiazomethane and HBF4. Dibutylstannylene compounds derived from benzyl -D-lactoside and its derivatives have been regioselectively benzylated. ° Similarly, 2,2 -di-0-alkyl-4,6 4 6 -di-0-benzylidene-Qt,a-trehaloses have been prepared by regioselective alkylation of a dibutylstannylene derivative. Phase transfer catalysed benzylation... 

Diphosphine pincer-type PCP-rhodium complexes were found to be robust precursors for the synthesis of carbene complexes such as 311 and 312 by reaction with phenyldiazomethane. ... 

General methods for the synthesis of a-arylsulphonyl- and a-alkanesulphonyl phenyldiazomethanes have been surveyed. ... 

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