Three-Membered Ring Heterocycles

Ram, Vishnu Ji; Sethi, A. S.; Nath, Mahendra; Pratap, Ramendra

doi:10.1016/b978-0-08-101033-4.00003-6

Cited by 6 publications

(2 citation statements)

References 223 publications

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“…This non-zero value and deviation from thermoneutrality is taken in the current paper as the strain energy of aziridine. This value for aziridine is numerically close to those for the corresponding hydrocarbon and cyclic ether, cyclopropane (116 kJ/mol) and ethylene oxide (oxirane) (114 kJ/mol), respectively, and so this 118 kJ/mol is consistently identified as the strain energy of aziridine [Eq (6), (7)]. cyclopropane…”

Section: Interrelations Of the Strain Energies Of Isomeric Azirines A...mentioning

confidence: 62%

“…In fact, substituted derivatives of 2H-azirine (3) can be found in natural products. [7] Other derivatives of 3 have been used as a source of nitrile ylides on photolysis which is of itself a useful starting point to generate heterocycles such as pyrrolines [8] by 1,3-dipolar addition to dipolarophiles. Similarly, 1-azabicyclobutanes 2 are well-established synthetic precursors of azetidines and other heterocycles.…”

Section: Introductionmentioning

confidence: 99%

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Strained Small Nitrogen Heterocycles‐Azabicyclobutanes and Azirines

et al. 2023

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Small ring nitrogen heterocycles, azabicyclobutanes and azirines, were investigated by computational methods in order to address the discrepancy between their regioisomers 1‐ and 2‐azabicyclobutane and 1H‐ and 2H‐azirines. Both 1‐azabicyclobutane and 2H‐azirine are well known synthetic starting points to larger nitrogen heterocycles whereas 2‐azabicyclobutane and 1H‐azirine and their derivatives have yet to be reported as isolable compounds. Calculated parameters such as structure, base strength (proton affinities), NICS values and enthalpies of formation from which strain energies are derived are reported. The destabilization of the less stable regioisomers is attributed to homoantiaromaticity in 2‐azabicyclobutane and antiaromaticity in 1H‐azirine. Two stereoisomers exist for 2‐azabicyclobutane with the endo‐ stereoisomer being more stable. This phenomenon is indicative of the hydrogen bond acceptor properties of the neighboring cyclpropane and the π‐bond character of the central bond in 2‐azabicyclobutane.

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Section: Interrelations Of the Strain Energies Of Isomeric Azirines A...mentioning

confidence: 62%

Section: Introductionmentioning

confidence: 99%

Strained Small Nitrogen Heterocycles‐Azabicyclobutanes and Azirines

et al. 2023

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Epoxy Compounds—Olefin Oxides (Ethylene Oxide, Propylene Oxide, and Miscellaneous Oxides)

Klapacz

Doskey

2023

Patty's Toxicology

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This chapter discusses the chemistry, uses, health information, and industrial hygiene handling procedures of epoxides, that is, substances containing strained, three‐membered rings with two adjacent carbons and one oxygen atom. This functionality underlies epoxides' high reactivity, physicochemical properties, and toxicity. The majority of the content is dedicated to ethylene oxide and propylene oxide, but other epoxides are also of industrial interest and are described here; their databases have evolved over the last couple of decades and this new understanding is highlighted here. These are 1,2‐butylene oxide, 2,3‐epoxybutane, butadiene diepoxide, vinylcyclohexene monoxide, vinylcyclohexene dioxide, and styrene oxide.

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