Catalytic control of reactions of dipoles and carbenes; 1 an easy and efficient synthesis of cycloheptatrienes from aromatic compounds by an extension of Buchner's reaction
Anciaux, A. J.; Demonceau, Albert; Hubert, André J.et al.
1980 • In Journal of the Chemical Society. Chemical Communications, (16), p. 765-766
[en] Rhodium salts from strong carboxylic acids [particularly rhodium(II) trifluoroacetate] are novel and highly efficient catalysts for the preparation of substituted cycloheptatriene carboxylates from aromatic hydrocarbons and diazo-esters, and in contrast with the classical Buchner procedures these rhodium catalysts lead specifically to the 1-isomer (3), avoiding its subsequent prototropic conversion into conjugated isomers.
Disciplines :
Chemistry
Author, co-author :
Anciaux, A. J.; Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liège, Sart Tilman, 4000 Liege, Belgium
Demonceau, Albert ; Université de Liège - ULiège > Département de chimie (sciences) > Chimie macromoléculaire et catalyse organique
Hubert, André J.
Noels, Alfred ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Petiniot, N.; Laboratory of Macromolecular Chemistry and Organic Catalysis, University of Liège, Sart Tilman, 4000 Liege, Belgium
Teyssié, Philippe ; Université de Liège - ULiège > Relations académiques et scientifiques (Sciences)
Language :
English
Title :
Catalytic control of reactions of dipoles and carbenes; 1 an easy and efficient synthesis of cycloheptatrienes from aromatic compounds by an extension of Buchner's reaction
Publication date :
1980
Journal title :
Journal of the Chemical Society. Chemical Communications
For Part 1 and references to related publications see A J Anciaux, A J Hubert, A F Noels, N Petiniot and Ph Teyssie J Org Chem, 1980, 45 695
N Petimot, A J Anciaux, A F Noels, A J Hubert and Ph Teyssie Tetrahedron Lett 1978 1239
For general references on Buchner synthesis and diazo ester reactions see V Dave and E W Warnhoff Org React 1970, 18 217
D S Wulfman, G Lmstrumelle and C F Cooper Synthetic Application of Diazoalkanes Diazocyclopentadienes and Diazo azacyclopentadienes Vol II, ed S Patai Wiley-Interscience New York 1978 ch 18
D S Wulfman and B Poling, Reactive Intermediates, Vol 1, ed R A Albramovitch, Plenum Press, London-New York, 1980, ch 5
D Lloyd, ‘Carboxylic Non benzenoid Aromatic Compounds Elsevier Amsterdam 1966 pp 122 and 125
See also the striking influence of the trifluoroacetate ion m Ni catalysed polymerisation of butadiene Ph Teyssie, A Devaux, P Hadijandreou, M Julemont, J M Thomassm, E Walckiers, and R Warm, Preparation and Properties of Stereoregular Polymers eds R W Lenz and F Ciardelli, Reidel Dordrecht 1980, p 131
A J Hubert, A F Noels, and Ph Teyssie, unpublished results
