Oxidation of vanillins with thallium(III) nitrate. An exercise in NMR spectroscopy and photochemistry

S. Antus, M. Nógrádi, E. Gács-Baitz, L. Radics, H. D. Becker, B. Karlsson, A. M. Pilotti

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Oxidation of isovanillin, vanillin and o-vanillin with TI(NO3)3 in MeOH gave the dimethyl acetals of 6,6-dimethoxy-2,4-cyclohexadien-1-one aldehydes (4-6 which dimerized spontaneously to give a single product each (7-9) the structure of which was elucidated by 1H and 13C NMR, photocyclization to the cage compounds 12-14 and of 7 and 9 by X-ray diffraction as well.

Original languageEnglish
Pages (from-to)2573-2577
Number of pages5
JournalTetrahedron
Volume34
Issue number16
DOIs
Publication statusPublished - 1978

Fingerprint

Photochemistry
Thallium
Photochemical reactions
Aldehydes
X-Ray Diffraction
Nitrates
Nuclear magnetic resonance spectroscopy
Magnetic Resonance Spectroscopy
Nuclear magnetic resonance
X ray diffraction
Oxidation
1,1-dimethoxyethane
2-vanillin
isovanillin
vanillin
Proton Magnetic Resonance Spectroscopy
Carbon-13 Magnetic Resonance Spectroscopy
thallium nitrate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Oxidation of vanillins with thallium(III) nitrate. An exercise in NMR spectroscopy and photochemistry. / Antus, S.; Nógrádi, M.; Gács-Baitz, E.; Radics, L.; Becker, H. D.; Karlsson, B.; Pilotti, A. M.

In: Tetrahedron, Vol. 34, No. 16, 1978, p. 2573-2577.

Research output: Contribution to journalArticle

Antus, S. ; Nógrádi, M. ; Gács-Baitz, E. ; Radics, L. ; Becker, H. D. ; Karlsson, B. ; Pilotti, A. M. / Oxidation of vanillins with thallium(III) nitrate. An exercise in NMR spectroscopy and photochemistry. In: Tetrahedron. 1978 ; Vol. 34, No. 16. pp. 2573-2577.
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AU - Pilotti, A. M.

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