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Kolesnik, V. D.; Ткачев, А. В.

doi:10.1023/a:1023902621846

Cited by 6 publications

(3 citation statements)

References 5 publications

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“…Research carried out so far has focused on the reactivity of carvone O ‐methyl oxime with dibenzylphosphine oxide, nitrosyl chloride and iridium catalysts towards amidation of the unactivated methyl groups . Some studies regarding SOR of simple cyclic and acyclic oxime ethers have been done by the International Flavors and Fragrances and Givaudan…”

Section: Introductionmentioning

confidence: 67%

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Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

Strub

Kula

Sikora

et al. 2015

Flavour & Fragrance J

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Novel semi‐synthetic fragrant compounds were prepared from both isomers of carvone. Deprotonation of (+) and (−)‐carvone oximes with sodium hydride and subsequent O‐Alkylation with various alkyl halides in DMSO resulted in 18 ethers. Scents of most synthesized compounds are agreeable. A shift of fragrance is observed between substrates. The scent of (−)‐carvone resembles that of spearmint and (+)‐carvone – caraway. The fragrance of carvone oximes is similar, vegetable‐like. Significant differences were observed between homologous series of carvone oxime ethers. Their odours range from vegetable‐like (pickled cucumber, leaves of horseradish and carrot, scallion and onion) and herbaceous to sulphuric, floral (lily) and fruity (blackcurrant and pear). Copyright © 2015 John Wiley & Sons, Ltd.

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Section: Introductionmentioning

confidence: 67%

“…Yield 77%, b.p. = 80 °C (2.5 mbar); [α] D 25 = −62 (c 1.0, CHCl 3 ; lit . ‐13.3, c 2.0, CHCl 3 ), vegetable, radish, leaves of horseradish, pickled cucumbers (after 10 min) fragrance…”

Section: Methodsmentioning

confidence: 99%

Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

Strub

Kula

Sikora

et al. 2015

Flavour & Fragrance J

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“…Synthesis of (1R,5R,E)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptan-3-one O-methyl Oxime (1) [58] In a 500 mL flask, pinocarvone oxime (15.6 g, 95,0 mmol), tetrabutylammonium hydrogen sulfate (0.644 g, 1.89 mmol) and sodium hydroxide (5.69 g, 142 mmol) in benzene/DMSO (200 ml/20 ml) were added, and the reaction was stirred at room temperature for 0.5 h. Then, dimethyl sulfate (14.3 g, 114 mmol) was added to one portion, after which it was stirred at room temperature for an additional 48 h (monitored by TLC). The reaction mixture was diluted with H 2 O (200 mL) and extracted with benzene (1×100 mL).…”

Section: Methodsmentioning

confidence: 99%

Unusual Ring Opening of Bicyclic Terpenes During Pd‐Catalyzed Coupling with Aromatic Halides

Shutovskaya,

Ustimenko,

Tkachev

et al. 2023

Adv Synth Catal

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Herein we describe Pd‐catalyzed cross‐coupling reaction of α‐pinene derivative – pinacarvone O‐methyl oxime (1) with aryl halides (2). Surprisingly, the formation of the C−C coupling product was accompanied by an unexpected opening of the pinene bicyclic structure. The (Z)‐2‐aryl‐4,4,5‐trimethylcyclohexa‐2,5‐dien‐1‐one O‐methyl oxime (3) was formed as the resulting product. The reaction conditions of the developed synthetic procedure were carefully optimized and the reaction mechanism was supposed on the basis of data obtained by structural and computational methods.

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Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

Palácios

Santos

Vicario

et al. 2010

Patai's Chemistry of Functional Groups

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This comprehensive chapter, organized in three different sections, includes new topics focused on preparation and synthetic applications of phosphorus functionalized hydroxylamines, oximes and hydroxamic acids. The first section comprises the synthesis of phosphorus O ‐substituted hydroxylamines either through phosphorus‐oxygen or nitrogen‐oxygen single bond formation. The synthesis of N ‐substituted hydroxylamines is also covered in this first section by means of phosphorus‐nitrogen or carbon‐nitrogen bond formation reactions. This section also includes several transformations of phosphorus substituted hydroxylamines including among others: rearrangement, hydrolysis, reduction and oxidation reactions. Functionalized oximes containing phosphorus substituents including O ‐ and C ‐substituted oximes, and oximes with α‐ and β‐phosphorated moieties are covered in a second section. This provides an introduction to the common approaches to synthesize phosphorus substituted oximes, and the application of phosphorated oximes to the preparation of more elaborated compounds have been described. Some of the synthetic applications methods covered in the second section are fragmentation and rearrangement reactions, nucleophilic substitution at the phosphorus atom, intramolecular reactions, radical reactions, reduction of carbon‐nitrogen double bond, oxidation reactions, olefination reactions, dehydratation of oximes. The third section is dedicated to the synthesis and reactivity of phosphorus O ‐, N ‐, and C ‐substituted hydroxamic acid derivatives, spanning the few reports in the literature covering this topic. An extensive and current list of references and a subject index complete the chapter. Phosphorus Substituted Hydroxylamine Derivatives Phosphorus Substituted Oximes Phosphorus Substituted Hydroxamic Acid Derivatives Acknowledgments

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Untitled

Cited by 6 publications

References 5 publications

Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

Synthesis and olfactory evaluation of homologous series of (+)‐ and (−)‐carvone oxime ethers

Unusual Ring Opening of Bicyclic Terpenes During Pd‐Catalyzed Coupling with Aromatic Halides

Phosphorus Derivatives of Hydroxylamines, Oximes and Hydroxamic Acids

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