In addition to the literature in the link below, there is a lot of literature about this compound(1,2-Benzisoxazole)Application In Synthesis of 1,2-Benzisoxazole, illustrating the importance and wide applicability of this compound(271-95-4).
The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Benzisoxazoles. III》. Authors are Borsche, Walther; Scriba, Wilhelm.The article about the compound:1,2-Benzisoxazolecas:271-95-4,SMILESS:C12=CC=CC=C1ON=C2).Application In Synthesis of 1,2-Benzisoxazole. Through the article, more information about this compound (cas:271-95-4) is conveyed.
cf. C. A. 33, 8197.5. Meyer (Cathcart and M., Ber. 25, 3291 (1892)) was of the opinion that benzisoxazoles could not be prepared from oximes of o-acylated halo- or nitrobenzenes unless the radical XC6H4C(:NOH) is bound with a neg. group. It is now shown that this is not true. o-BrC6H4CN and MeMgI give 85% of 2-BrC6H4Ac, b16 118-20°; oxime (I), m. 129°. 2-BrC6H4CO2Me and MeMgI give some dimethyl-2-bromophenylcarbinol, b16 128-30°; BrC6H4Ac was not formed. Heating I with KOH in 50% MeOH gives 80% of 3-methylbenzisoxazole, b15 104-8°. o-BrC6H4CN and EtMgBr give 90% of 2-bromopropiophenone, yellowish oil, b16 135-40°; 2,4-dinitrophenylhydrazone, orange-yellow, m. 115-16°; oxime, b16 164-72°; with KOH in 50% MeOH (9 h. at 120°) there results a mixture of unchanged oxime and ethylindoxazene. o-BrC6H4CN (18.2 g.) and PhCH2MgCl give about 12 g. of 2-bromophenyl benzyl ketone, b15 206-8° (2,4-dinitrophenylhydrazone, orange, m. 149°; oxime, m. 116°); KOH in 50% MeOH (8 h. at 110-15°) gives 85% of 3-benzylbenzisoxazole, m. 87°. 4,3-Br(H2N)C6H3Me gives about 70% of 3-cyano-4-bromotoluene, m. 65°; MeMgI gives 3-acetyl-4-bromotoluene, b15 132-6°; 2,4-dinitrophenylhydrazone, orange, m. 170°; oxime, m. 131-2° (cf. Claus, J. prakt. Chem. 46, 26(1892), who states that it could not be converted to II); KOH in 50% MeOH (9 h. at 150°) gives 3,5-dimethylbenzisoxazole (II), b14 116-18° (NO2 derivative, m. 72°). 2-ClC6H4CN (6.4 g.) gives 4 g. 2-ClC6H4Ac; 2,4-dinitrophenylhydrazone, dark yellow, m. 206°; semicarbazone, m. 178-9°. 2-BrC6H4Ac, BzH and 10% NaOH in MeOH give 2-cinnamoylbromobenzene, b14 234-8°, as a yellow, viscous oil; 2,4-dinitrophenylhydrazone, red, m. 236-7°; an oxime could not be prepared 6,3-Br (O2N)C6H3Ac (4.88 g.) and 4 g. PhNHNH2.HCl in MeOH, heated 18 h. at 150°, give 3.1 g. of 3-methyl-1-phenyl-5-nitroisoindazole, yellow, m. 131-2°; catalytic reduction gives the 5-NH2 derivative, m. 127-8° (Bz derivative, m. 160-1°); a byproduct, yellow, m. 336°, is probably the corresponding azoxy compound Removal of the NH2 group gives 3-methyl-1-phenylisoindazole, m. 73-4°.
In addition to the literature in the link below, there is a lot of literature about this compound(1,2-Benzisoxazole)Application In Synthesis of 1,2-Benzisoxazole, illustrating the importance and wide applicability of this compound(271-95-4).
Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI