Ring-chain tautomerism of 2-alkylamino-substituted tetrahydropyrans and tetrahydrofurans

Потехин, А. А.; Zhdanov, S. L.

doi:10.1007/bf00471897

Cited by 3 publications

(2 citation statements)

References 2 publications

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“…The tertiary amine 33a liberated isobutene under relatively mild conditions to generate an equilibrating mixture of the known secondary amine 37a and the imine 37b (Scheme ). Presumably, the primary alcohol 33b and its protic properties are responsible for the ease of the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…The latter assumption is based on comparing the analogous secondary amines and the fact that the nucleophilicity of di-tert-amylamine in the presence of the electrophile allenyl isothiocyanate is lower than that of tert-butyl-tert-octylamine. 9 The tertiary amine 33a liberated isobutene under relatively mild conditions to generate an equilibrating mixture of the known 18 secondary amine 37a and the imine 37b (Scheme 7).…”

Section: ■ Introductionmentioning

confidence: 99%

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Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction

et al. 2020

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A number of amines with three bulky alkyl groups at the nitrogen, which surpass the steric crowding of triisopropylamine considerably, were prepared by using different synthetic methods. It turned out that treatment of N-chlorodialkylamines with organometallic compounds, for example, Grignard reagents, in the presence of a major excess of tetramethylenediamine offered the most effective access to the target compounds. The limits of this method were also tested. The trialkylamines underwent a dealkylation reaction, depending on the degree of steric stress, even at ambient temperature. Because olefins were formed in this transformation, it showed some similarity with the Hofmann elimination. However, the thermal decay of sterically overcrowded tertiary amines was not promoted by bases. Instead, this reaction was strongly accelerated by protic conditions and even by trace amounts of water. Reaction mechanisms, which were analyzed with the help of quantum chemical calculations, are suggested to explain the experimental results.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction

et al. 2020

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Oxime ether analogs of sex pheromone components of turnip moth (Agrotis segetum Schiffermüller)

Martin

Weber

1994

J Chem Ecol

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Oxime ether analogs of sex pheromone components of the turnip moth (Agrotis segetum Schiff.) were synthesized by the acidolytic opening of cyclic enol ethers withO-alkyl hydroxylamine hydrochlorides. The compounds varying in chain lengths and in the position of the C=N double bond were studied by electrophysiological single sensillum recordings (electrosen-sillography: ESG). The ESG data indicate in general reduced receptor interaction of all analogs investigated in comparison with natural pheromone components of the turnip moth. The data also show that the grade of decrease of receptor interaction depends on specific structural changes within the molecule. The results demonstrate high complementary pheromone-receptor relationships, predominantly depending on the position of the unsaturated group in the chain, whereas analogs with other structural changes are still recognized as a pheromone-like compound by the receptor.

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A unique urinary constituent, 6-hydroxy-6-methyl-3-heptanone, is a pheromone that accelerates puberty in female mice

Novotný

Jemioło

Wiesler

et al. 1999

Chemistry & Biology

114

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The male house mouse excretes into its urine a large quantity of a volatile substance that has a unique lactol/hydroxyketone structure. This substance is capable of binding to the less volatile urinary constituents, such as proteins or peptides, and is active in puberty-acceleration bioassays. The controversies regarding the volatility of the puberty-accelerating pheromones can now be explained by considering a complex of volatile lactol/hydroxyketone and urinary proteins.

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Ring-chain tautomerism of 2-alkylamino-substituted tetrahydropyrans and tetrahydrofurans

Cited by 3 publications

References 2 publications

Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction

Synthesis of Trialkylamines with Extreme Steric Hindrance and Their Decay by a Hofmann-like Elimination Reaction

Oxime ether analogs of sex pheromone components of turnip moth (Agrotis segetum Schiffermüller)

A unique urinary constituent, 6-hydroxy-6-methyl-3-heptanone, is a pheromone that accelerates puberty in female mice

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