Novel synthesis of α-nitroalkenes from nitroalkanes via halogenation of intermediate N,N-bis(silyloxy)enamines

Kunetsky, Roman A.; Dilman, Alexander D.; Стручкова, Марина И.; Tartakovsky, Vladimir A.; Ioffe, Sema L.

doi:10.1016/j.tetlet.2005.05.113

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Nitrones and Nitronates As α‐C‐nucleophilic Synthons2

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Cited by 12 publications

(3 citation statements)

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“…Nitromethane (nitroalkane) also had a dual role, that is, as the solvent and as the substrate. In view of this, the suggested pathway for the reaction (C–S bond formation) is through the formation of a silyl nitronate (Scheme ) , , …”

Section: Resultsmentioning

confidence: 99%

Highly Efficient One‐Step Synthesis of N‐Trimethylsiloxy Alkyl Imidothioates

Kuciński

Hreczycho

2016

Eur J Org Chem

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A hitherto unknown synthetic pathway for the synthesis of N‐trimethylsiloxy alkyl imidothioates has been presented. The catalyst‐free route uses a range of aromatic, aliphatic, and heterocyclic thiols in the presence of nitroalkanes and hexamethyldisilazane (HMDS). This unusual method expands upon the knowledge of nitro compounds and demonstrates their importance not only as solvents but also as valuable organic reagents. This reaction proceeds under mild conditions and is characterized by excellent yields and a facile workup.

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Section: Resultsmentioning

confidence: 99%

Highly Efficient One‐Step Synthesis of N‐Trimethylsiloxy Alkyl Imidothioates

Kuciński

Hreczycho

2016

Eur J Org Chem

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“…Apart from C‐nucleophiles, some heteroatom‐based electrophiles such as halogens and arylsulfenyl chlorides also successfully underwent reaction with N , N ‐bis(oxy)enamines 13 and 15 . Reactions with these electrophiles do not require the addition of any Lewis acids.…”

Section: Nitrones and Nitronates As α‐C‐nucleophilic Synthonsmentioning

confidence: 99%

“…The reaction of N , N ‐bis(siloxy)enamines 13 with molecular bromine or iodine in the presence of tetrabutylammonium acetate at −78 °C affords conjugated nitroalkenes 70 (Scheme ) . These products are formed by the fast elimination of the TMS group from transient α‐halo‐substituted nitronates 69 under the action of the acetate anion.…”

Section: Nitrones and Nitronates As α‐C‐nucleophilic Synthonsmentioning

confidence: 99%