Conformational and configurational chirality of 1,2-dimethylaminoalkylformylcymantrenes. Molecular structure and absolute configuration of (−)578-1-[α-(N,N-dimethylamino)ethyl]-2-formylcymantrene

Loim, N. M.; Laryukova, M.V.; Andrianov, V. G.; Tsiryapkin, V.A.; Парнес, З. Н.; Struchkov, Yu. T.

doi:10.1016/s0022-328x(00)98850-8

Cited by 11 publications

(2 citation statements)

References 12 publications

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“…Solutions of 1-cymantrenylethyl azide [35] (4.7 g, 19 mmol) in acetonitrile (10 mL) and phenylacetylene (2.9 g, 28.5 mmol) in acetonitrile (10 mL) were then successively added, and the reaction mixture was stirred at room temperature for 24 h. Then the reaction mixture was passed through a silica gel layer. The dark red solution turned sandy in color.…”

Section: -(1-cymantrenylethyl)-4-phenyl-123-triazole (21)mentioning

confidence: 99%

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

et al. 2016

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The synthesis of four new 1,2,3‐triazole derivatives and seven 1,2,3‐triazolium salts that contain an organometallic group (i.e., cymantrenyl and ferrocenyl) at either the N‐1, N‐2, or N‐3 position was realized. The alkylation of organometallic and organic triazole derivatives was investigated, and as a result of these studies, it was found that the presence of a good leaving group at the heterocyclic nitrogen atom led to transalkylation and subsequent migration of the N‐1 substituent to the N‐2 position of the triazole moiety. The nucleophilicity of the counterion of the triazolium salt influenced the transalkylation and isomerization processes, which suggests that the elimination of the N‐substituent most likely occurs though a concerted mechanism with nucleophilic assistance from the counterion. Thus, a new approach to the synthesis of 2,4‐disubstituted 1,2,3‐triazoles has been developed.

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Section: -(1-cymantrenylethyl)-4-phenyl-123-triazole (21)mentioning

confidence: 99%

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

et al. 2016

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“…The signals for the α‐ and β‐protons of the Cp ring were assigned by using phase‐sensitive 2D NOESY, as well as comparing with the NMR spectra of deuterated analogues. These deuterated compounds were prepared from α‐deuteriocymantrenecarbaldehyde14 and 1‐( N , N , N ‐trimethylammonium)ethyl(α‐deuteriocymantrene) iodide ( 12 )13,15 according to Scheme .…”

Section: Methodsmentioning

confidence: 99%

Investigation of the Photochemical Behaviour of Tricarbonyl(cyclopentadienyl)manganese Derivatives with Carbamate Groups

et al. 2009

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Chiroptical Properties of Compounds ContainingCOGroups

Boiadjiev

Lightner

2009

Patai's Chemistry of Functional Groups

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Introduction The Octant Rule Compilation of Ketone and Aldehyde CD Unsaturated Ketones Compilation of Unsaturated Ketone and Aldehyde CD Exciton Chirality Addendum Acknowledgments

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Conformational and configurational chirality of 1,2-dimethylaminoalkylformylcymantrenes. Molecular structure and absolute configuration of (−)578-1-[α-(N,N-dimethylamino)ethyl]-2-formylcymantrene

Cited by 11 publications

References 12 publications

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

Transalkylation and Migration of N‐Substituent upon Alkylation of 1,2,3‐Triazoles Containing Good Leaving N‐Substituents

Investigation of the Photochemical Behaviour of Tricarbonyl(cyclopentadienyl)manganese Derivatives with Carbamate Groups

Chiroptical Properties of Compounds ContainingCOGroups

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