Mass spectrometry in structural and stereochemical problems. CLXXIX. Electron impact induced rearrangements of 1-phenylheptenes. Further evidence for double bond lability

Djerassi, Carl; Gerrard, A. F.

doi:10.1021/ja01052a045

Cited by 23 publications

(4 citation statements)

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“…This phenomenon is well documen-ted in the literature. [18] In 1969 Gerrard and Djerassi investigated the EI mass spectra of a series of isomeric phenylheptenes and found that they exhibited double bond mobility upon electron impact and therefore all isomers showed nearly identical mass spectra. The examined 1-phenylheptenes underwent skeletal and hydrogen rearrangements; for instance, the base peak [M -C 4 H 9 ]…”

Section: Characterisation Of the Reaction Products In The Solutionmentioning

confidence: 99%

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

et al. 2010

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Square planar arenido-(triphenylphosphane)nickel(II) complexes (3) containing a N,O-chelate ligand are catalysts for the carbon monoxide/ethene copolymerisation reaction. Pathways for catalyst deactivation have been elucidated by investigating the reactions of such complexes with aliphatic unsaturated compounds like olefins and alkynes. We have shown that the double or triple bond, respectively, inserts into the nickel-carbon bond followed by β-hydride elimination resulting in aryl-substituted olefins and allenes, which

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Section: Characterisation Of the Reaction Products In The Solutionmentioning

confidence: 99%

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

et al. 2010

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“…m/z=104 mass chromatograms show a sequence of peaks corresponding to a series of alkenyl benzenes. m/z= 104 ion [C 6 H 5 CH═CH 2 ] + is a prominent peak in alkenyl benzenes mass spectra, arising essentially from the rearrangement of two other fragment ions (m/z=174 and 145) [15]. The profile presented by this alkenyl benzenes series is different for each kind of lacquer and this allows distinguishing between the three types.…”

Section: Lacquer Py-gc/ms Analysismentioning

confidence: 99%

Applying pyrolysis-gas chromatography/mass spectrometry to the identification of oriental lacquers: study of two lacquered shields

Frade

Ribeiro

Graça³

et al. 2009

Anal Bioanal Chem

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Oriental lacquers have been used as coating materials for thousands of years for wooden, ceramics, leather and metal objects. Lacquers are natural polymers obtained from three species growing in different regions of Asia: Rhus vernicifera (China, Japan and Korea); Rhus succedanea (Vietnam and Taiwan); and Melanorrhoea usitate (Myanmar and Thailand). The identification of lacquer films is important for conservation and restoration purposes, as well as for art history studies because it may help in determining the origin of the lacquered objects. In this work, pyrolysis-gas chromatography/mass spectrometry using a filament-type pyrolyser was successfully applied to the characterization of oriental lacquers. A method to identify the three kinds of lacquer was developed and applied to the study of two lacquered shields imported from Asia in the sixteenth century. The materials that constitute the shields were also examined by Fourier-transform infrared microspectroscopy and details of the lacquering technique are reported.

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“…In order to explain this apparent anomaly it is necessary to invoke a mechanism such as that shown in Scheme 3 for the decomposition of 11. Initial benzylic cleavage followed by a 1,Zhydrogen (yJo + @ J. ac6H5 8 …”

Section: Peak At Mle 91mentioning

confidence: 99%

Mass spectrometry in structural and stereochemical problems—CLXXXV Effect of phenyl group in the mass spectra of trans‐10‐phenyl‐2‐decalone and trans‐10‐phenyldecalin

Gray

Djerassi

1970

Org. Mass Spectrom.

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With the use of deuterium labeling and metastable ion measurements, the major fragmentation pathways of trans-10-phenyl-2-decalone (11) have been deduced. A comparison with trans-10phenyldecalin (IV) demonstrated the almost complete domination of the phenyl group in directing the electron-impact promoted decomposition of 11. In fact, in contrast to the spectra of the methylated analogs, only one fragmentation pathway is uniquely associated with the carbonyl function. The substitution of a phenyl group at the ring junction in IV has permitted the recognition of definitive fragmentation pathways for this compound also. Such definition has not previously been possible for unsubstituted alicyclic hydrocarbons. The formation of an abundant tropylium ion from both

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Mass spectrometry in structural and stereochemical problems. CLXXIX. Electron impact induced rearrangements of 1-phenylheptenes. Further evidence for double bond lability

Cited by 23 publications

References 1 publication

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

Catalyst Deactivation by β‐Hydride Elimination: Olefin and Alkyne Insertion into Arenido–Nickel(II) Bonds

Applying pyrolysis-gas chromatography/mass spectrometry to the identification of oriental lacquers: study of two lacquered shields

Mass spectrometry in structural and stereochemical problems—CLXXXV Effect of phenyl group in the mass spectra of trans‐10‐phenyl‐2‐decalone and trans‐10‐phenyldecalin

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