ChemInform Abstract: Reaction of 3‐Thietanyl Isothiocyanate with Aliphatic Amines.

Allakhverdiev, M. A.; Alekperov, R. K.; Shirinova, N. A.; Akperov, N. A.

doi:10.1002/chin.200050112

Cited by 4 publications

(3 citation statements)

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“…Although it was claimed in [22] that the reaction of (chloromethyl)thiirane with ammonium thiocyanate leads to the formation of thietan-3-yl isothiocyanate we were unable to reproduce these results. Alkylation at the nitrogen atom by (chloromethyl)thiirane in an aqueous medium, which takes place with a thiirane-thietane rearrangement, is known for two types of heterocyclic systems-xanthines and benzimidazoles [23].…”

Section: Thiirane-thietane Rearrangementcontrasting

confidence: 67%

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Butkevich

Соколов

Томашевский

et al. 2007

Chem Heterocycl Compd

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Section: Thiirane-thietane Rearrangementcontrasting

confidence: 67%

Methods for the synthesis of derivatives of 3-aminothietane (Review)

Butkevich

Соколов

Томашевский

et al. 2007

Chem Heterocycl Compd

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“…2-(Chloromethyl)thiirane reacted with ammonium isothiocyanate to yield a mixture of 3-thietanyl isothiocyanate and 3-hydroxythietane [48,49] (Scheme 9). 3-Thietanyl isothiocyanate was further reacted with aliphatic amines to give quantitative yields of N-alkyl-N 0 -(thietan-3-yl)thioureas.…”

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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“…Electrophilic addition of SCl 2 [285], a mixture of POCl 3 (or POBr 3 )/thiobismorpholine [286] [290], sulfonamides [291] and phenates [291], or from (thiiran-2-yl)methanol under the conditions of the Mitsunobu reaction [292]. Addition of allyl lithium compounds with thiiranes gives rise to thietanes in good yields (Scheme 3.160) [293].…”

Section: Synthesis By Formation Of Two S-c Bondsmentioning

confidence: 99%