Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Journal of the American Chemical Society called Structural effects on rates and equilibriums. XVI. Effect of adjacent unshared electron pairs on ease of carbanion formation, Author is Hine, Jack; Dalsin, Philip D., which mentions a compound: 37443-42-8, SMILESS is O=C(C1OCCC1)OC, Molecular C6H10O3, Application of 37443-42-8.
The kinetics of NaOMe catalyzed D exchange of Me cyclopentanecarboxylate, two of its oxa derivatives and their acyclic analogs were studied in MeOD solution At 35° methyl cyclopentanecarboxylate exchanged 13 times as fast as Me α-ethylbutyrate, Me tetrahydro-2-furancarboxylate exchanged four times as fast as Me α-methoxybutyrate, and Me 1,3-dioxolane-2-carboxylate exchanged half as fast as Me dimethoxyacetate. From these results it was concluded that rates of carbanion formation may be decreased by repulsions between the unshared electron pairs of the carbanionic C atom and those of O atoms attached directly to it. Such repulsions may be minimized by appropriate rotation around the C-O bond in acyclic compounds but not as easily in cyclic compounds This electron repulsion effect operates in addition to the electronegativity effect, by which rates of formation of sp2-hybridized carbanions are slowed by highly electroneg. atoms attached directly to the site of carbanion formation. This interpretation of the results is analogous to that required to explain to explain recent observations on rates of pyramidal inversions at N and P.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics