Reactions of Amines. X. 1-t-Butyl-3-Phenylaziridinone

Baumgarten, Henry E.

doi:10.1021/ja00883a069

Cited by 55 publications

(13 citation statements)

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“…Whereas peroxy acids and hydrogen peroxide oxidize stable thioketenes to thioketene S-oxides (34)[321, nitrones of the I-pyrroline 1-oxide type ()N-+O) furnish a-thiolactones (35)[331. These compounds are of very recent date; the only reactions reported so far are the thermal decarbonylation and the spzC-S bond cleavage with nucleophilic reagents such as methanol and benzylamine (Scheme 6)[331.…”

Section: A-thiolactones (Thiiranones)mentioning

confidence: 99%

Heterocyclic Analogues of Methylenecyclopropanes

L'abbé

1980

Angew. Chem. Int. Ed. Engl.

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Heterocyclic three-membered rings with an exocyclic double bond merit special interest in view of their ring strain and their fascinating chemistry. Their synthesis, thermal decomposition, ring opening, and cycloaddition reactions will be discussed in this review. a-Lactams, alkylideneaziridines, diaziridinones, and diaziridinimines belong to the best known classes, but the chemistry of alkylideneoxiranes and -thiiranes, a-lactones, a-thiolactones, thiiranimines, and aziridinimines has also been studied to some extent. Two elusive three-membered rings are oxiranimines and thiaziridinimines; the former were postulated as reactive intermediates in the thermal decomposition of a-lactams, whereas the latter were trapped efficiently with double and triple bonds during thermolysis of N-sulfonyliminothiatriazolines. In spite of many attempts to prepare thione derivatives of the title compounds, they are still unknown. Included in this review are also some open-chain dipolar species which are isomeric with the heterocyclic three-membered rings.

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Section: A-thiolactones (Thiiranones)mentioning

confidence: 99%

Heterocyclic Analogues of Methylenecyclopropanes

L'abbé

1980

Angew. Chem. Int. Ed. Engl.

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“…Interest in α‐lactams dates back to 1962 when Baumgarten– first isolated and characterized the 1‐ t ‐butyl‐3‐phenylaziridinone B resulting from the base ( t ‐BuOK) mediated dehydrochlorination of N ‐chloro‐ N ‐ t ‐butyl phenylacetamide A (Scheme ). The physical data, together with the dual mode of ring cleavage following attack with O ‐nuclephiles, supported the α‐lactam structure even though the alternative structures (valence tautomers) could not be ruled out.…”

Section: Aziridinones Ring‐forming/ring‐opening Processesmentioning

confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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The aim of this review is to highlight the rich chemistry of α‐haloamides originally mainly used to discover new C−N, C−O and C−S bond forming reactions, and later widely employed in C−C cross‐coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical‐mediated transformations of α‐haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α‐halohydroxamate‐based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.

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“…CO Chart 1 depicts, in outline, a mechanism to encompass all the reactions involved in the action 'of sodium amide on a-haloamides. It assumes that the conversions Ia -+ IXa, Ib -+(IXb, Xb and XIb), Ie -e Xc, and Id -+ Xd, proceed via an intermediate (a-Iactam) whose structure can be represented essentially by either the aziridinone (II-III) or the oxirane (IV) forms (see [9], compare [10D. The latter forms, presumably highly reactive, undergo a nucleophilic attack by amide ions to give a negatively charged adduct (V) which may decompose, v i a ring-opening, to yield either VI or VII, depending on the structure.…”

Section: Analmentioning

confidence: 99%