Computed Properties of C5H4ClNO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Chloropyridine 1-oxide, is researched, Molecular C5H4ClNO, CAS is 2402-95-1, about Regiospecific thermal rearrangements of 2-allyloxypyridine N-oxides. Author is Alker, David; Mageswaran, Sivapathasuntharam; Ollis, W. David; Shahriari-Zavareh, Hooshang.
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 = CH2CCPh,CH2CH:CHPh) gave only [1,4]rearrangement products IV(R2 = CH2CCPh,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.
This literature about this compound(2402-95-1)Computed Properties of C5H4ClNOhas given us a lot of inspiration, and I hope that the research on this compound(2-Chloropyridine 1-oxide) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem