A small discovery about 2402-95-1

In addition to the literature in the link below, there is a lot of literature about this compound(2-Chloropyridine 1-oxide)Application of 2402-95-1, illustrating the importance and wide applicability of this compound(2402-95-1).

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 2-Chloropyridine 1-oxide( cas:2402-95-1 ) is researched.Application of 2402-95-1.Alker, David; Mageswaran, Sivapathasuntharam; Ollis, W. David; Shahriari-Zavareh, Hooshang published the article 《Regiospecific thermal rearrangements of 2-allyloxypyridine N-oxides》 about this compound( cas:2402-95-1 ) in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999). Keywords: allyloxypyridine oxide thermal rearrangement regiospecificity; sigmatropic rearrangement allyloxypyridine oxide; pyridine oxide allyloxy sigmatropic rearrangement. Let’s learn more about this compound (cas:2402-95-1).

On heating allyloxypyridine oxide I (R = CHMeCH:CH2) (II) in C2Cl4, pyridone derivative III (R1 = CH2CH:CHMe) (91%) was exclusively obtained in a [3:3]sigmatropic rearrangement. This is in contrast to an earlier report by J.E. Lister and H. Tickelman (1968) that II rearranged at room temperature in the absence of solvent to give isomeric pyridones IV (R2 = CHMeCH:CH2,CH2CH:CHMe) in 80% and 10% resp. Similarly on heating I (R = CH2CH:CHMe) in DMF the [3,3]sigmatropic rearrangement product III (R1 = CHMeCH:CH)2 was obtained in 62% yield together with 31% [1,4] product IV(R2 = CH2CH:CHMe). Thermal rearrangement of I(R = CH2CCPh,CH2CH:CHPh) gave only [1,4]rearrangement products IV(R2 = CH2CCPh,CH2CH:CHPh) in 91% and 80% resp. Thus only [1,4] and [3,3]sigmatropic rearrangements are observed in thermolysis of 2-allyloxypyridine N-oxides and this regiospecificity supports the view that these rearrangements proceed by concerted symmetry-allowed path-ways.

In addition to the literature in the link below, there is a lot of literature about this compound(2-Chloropyridine 1-oxide)Application of 2402-95-1, illustrating the importance and wide applicability of this compound(2402-95-1).

Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem