ChemInform Abstract: 3‐Aryloxythietanes as Admixtures to Lubricating Oils.

Allakhverdiev, M. A.; Akperov, N. A.; Фарзалиев, В. М.; Zeinalova, G. A.; Guseinova, A. T.

doi:10.1002/chin.198831136

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“…Similarly, salts of carboxylates [40][41][42], thiocarboxylates [43,44], and dialkyldithiophosphates [45,46] reacted with 2-(chloromethyl)thiirane, yielding the corresponding thietan-3-ylmethyl alkanoates, thietan-3-ylmethyl thiocarboxylates, and dialkyldithio thietan-3-ylmethyl phosphates, respectively. The corresponding thiirane derivatives were also obtained in some cases depending upon the reaction conditions (Scheme 7).…”

Section: Synthesis Of Four-membered Heterocycles By Ringmentioning

confidence: 99%

Synthesis of Four- to Seven-Membered Heterocycles by Ring Expansion: Ring Expansions of Thiiranes and Thietanes

2015

Topics in Heterocyclic Chemistry

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Thiiranes and thietanes are important intermediates in organic synthesis, just as their oxygen and nitrogen analogs (oxiranes and aziridines, and oxetanes and azetidines). They have been widely applied in the preparation of sulfur-containing compounds. Thiiranes undergo ring expansions to generate various four-, five-, six-, and seven-membered heterocyclic products, even larger heterocycles. Thietanes also undergo ring expansions to produce five-, six-, and seven-membered heterocyclic compounds, even larger heterocycles as well. The ring expansions include insertion, nucleophilic and electrophilic ring opening, and subsequent cyclization. The regioselectivities in nucleophilic ring-opening reactions of unsymmetrical thiiranes and thietanes are discussed. Generally, nucleophiles attack on the less substituted vicinal carbon atom to the sulfur in unsymmetrical thiiranes and thietanes, controlled by steric hindrance. In the presence of Lewis acids, the electronic effect significantly impacts the regioselectivity in ring-opening reactions. 2-Arylthiiranes and 2-alkenylthiiranes are attacked on their more substituted vicinal carbon atom with nucleophiles (the electronic effect control). For thietanes, electrophilic ring expansion is one of the major processes. Unsymmetrical thietanes undergo electrophilic ring expansion with carbenes and nitrenes through electrophilic attack and subsequent Stevens-type rearrangement, with the more substituted vicinal carbon shifting. Mechanisms on some of the most important ring expansions of thiiranes and thietanes are introduced.

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Section: Synthesis Of Four-membered Heterocycles By Ringmentioning

confidence: 99%

Synthesis of Four- to Seven-Membered Heterocycles by Ring Expansion: Ring Expansions of Thiiranes and Thietanes

2015

Topics in Heterocyclic Chemistry

View full text Add to dashboard Cite

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ChemInform Abstract: 3‐Aryloxythietanes as Admixtures to Lubricating Oils.

Cited by 1 publication

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Synthesis of Four- to Seven-Membered Heterocycles by Ring Expansion: Ring Expansions of Thiiranes and Thietanes

Synthesis of Four- to Seven-Membered Heterocycles by Ring Expansion: Ring Expansions of Thiiranes and Thietanes

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