Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Ariza‐Castolo, Armando; Godoy-Reyes, Joseantonio

doi:10.1002/(sici)1097-458x(199903)37:3<219::aid-mrc425>3.0.co;2-7

Cited by 9 publications

References 24 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Yazıcıoğlu

Ахмедов

Tanyeli

2008

Helvetica Chimica Acta

View full text Add to dashboard Cite

Alkylbenzenes are synthesized for the first time from aliphatic hydrocarbons via an one pot, transition metal‐free coupling approach under basic conditions. The method consists of two steps: condensation of 2‐bromoprop‐2‐enyl‐ or 2‐propargylcyclohexanone with alcohols, amines, or amino alcohols, followed by base treatment (Scheme 1). Phenolic ethers and N‐phenylated polyalkyl aromatic compounds are shown to be in the scope of the demonstrated reaction (Table). The proposed mechanism suggests that the unsaturation in another part of the molecule (propargyl‐group equivalent) is transferred into the cyclohexane ring to yield a benzene ring through a series of prototropic shifts.

show abstract

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Yazıcıoğlu

Ахмедов

Tanyeli

2008

Helvetica Chimica Acta

View full text Add to dashboard Cite

show abstract

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Guerrero‐Álvarez

Moncayo-Bautista

Ariza‐Castolo

2004

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

The relative configuration of 11 1,4-diazaspiro[4.5]decanes (1a-1j and 1m), 15 1,4-oxazaspiro[4.5]decanes (2a-2o) and 10 1,4-dioxaspiro[4.5]decanes (3a-3n) substituted at the 2-, 6-, 7- or 8-position by a methyl group or using the tert-butyl group as a model for the ananchomeric structure is reported. The relative stereochemistry was analyzed by 1H, 13C, 15N and 17O NMR and all isomers present were characterized spectroscopically. Compounds with a methyl group in the six-membered ring show a chair conformation preference with the methyl group in the equatorial position. Compounds with one or two nitrogens exhibit a tautomeric equilibrium between the imine-diazolidine forms, as demonstrated by IR and 13C NMR.

show abstract

Relative acidities and structure analysis of cis and trans isomers of 1,5‐oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance

Guerrero‐Álvarez

Mas-Ku

Garcías-Morales

et al. 2010

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

The relative acidities of the cis and trans isomers of a series of 1,5-oxazaspiro[5.5]undecane derivatives were determined by measuring DeltapK in acid-base titrations followed by (1)H NMR. Relative structural stabilities were determined by measuring substituent chemical shift and gamma-gauche effects in (13)C, (15)N, and (17)O NMR. Crystallographic characterization of a model spiro[5.5]undecane is presented to support the basicity in solid state.

show abstract

Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Cited by 9 publications

References 24 publications

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR

Relative acidities and structure analysis of cis and trans isomers of 1,5‐oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance

Contact Info

Product

Resources

About

Stereochemical arrangement of spiro[4.5]decane derivatives by15N and17O NMR spectroscopy

Cited by 9 publications

References 24 publications

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Base Mediated Aromatization of Carbonyl Condensation Products Derived from 2‐(2‐Bromoprop‐2‐enyl)cyclohexanone Derivatives via ‘Intramolecular Unsaturation Transfer’

Assignment of the relative configuration of spiro[4.5]decanes by 13C, 15N and 17O NMR

Relative acidities and structure analysis of cis and trans isomers of 1,5‐oxazaspiro[5.5] undecane derivatives by multinuclear magnetic resonance

Contact Info

Product

Resources

About

Assignment of the relative configuration of spiro[4.5]decanes by ¹³C, ¹⁵N and ¹⁷O NMR