Reaction between dimethyloxosulfonium methylide and benzonitrile oxide was written by Umani-Ronchi, A.;Bravo, P.;Gaudiano, G.. And the article was included in Tetrahedron Letters in 1966.SDS of cas: 80348-66-9 The following contents are mentioned in the article:
The reactivity of H2C–S+(O)Me2 (I) towards 1,3-dipoles was investigated to test the possibility of obtaining 4-membered heterocyclic rings. (I prepared in situ from Me3S(O)I or Me3S(O)Cl and NaH) treated with PhCNO in cold Me2SO gave a complex mixture from which 3-phenyl-2-isoxazoline (II), Ph vinyl ketone oxime (III), 3-phenyl-5-benzoyl-2-isoxazoline oxime (IV) and the Ph vinyl ketone oxime hydroxamie ester (V) were isolated. None of the unstable 3-phenyloxazetidine (VI) was isolated. The ylide brought about 2 consecutive transfers of CH2 to the substrate, probably through the zwitterion intermediate (VII) from which the compounds II-V may be readily derived. II was identified by anal., N.M.R. spectrum, and physicochem. characteristics. Addition of 2 molar equivalents I per molar equivalent PhNCO yielded up to 30% III, m. 85°, evidently the syn-Ph isomer. IV, m. 136°, was prepared by reaction of III with PhCNO. V, m. 126°, was also obtained in very small amount in the reaction of PhCNO with III. Beside the compounds II-V, many byproducts were obtained in small amounts PhCN, BzNH2 and BzOH originated from PhCNO by reductive and hydrolytic processes. The diphenylfuroxan (VIII) is a normal product of dimerization; BzNHOBz is a decomposition product of PhC(:NOH)Cl as well as of PhCNO itself under acid conditions: and the diphenyl-1,2,4-oxadiazole (IX) represents the product of the reaction between PhCNO and PhCN (CA 51, 15502e) according to Leandri and Pellotti. This study involved multiple reactions and reactants, such as Isoxazol-4-ol (cas: 80348-66-9SDS of cas: 80348-66-9).
Isoxazol-4-ol (cas: 80348-66-9) belongs to isoxazole derivatives. Isoxazoles are aromatic heterocycles containing an N–O bond. Isoxazoles are commonly used as enaminoketone or β-diketone surrogate. The electrophilic cyclization of various 2-alkynone O-methyl oximes with a wide range of substrates such as ICl, I2, Br2, PhSeBr, etc. provides a variety of 3,4,5-trisubstituted isoxazoles in good to excellent yields.SDS of cas: 80348-66-9
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem