229. Colchicine and related compounds. Part VII

Cook, J. W.; Dickson, G. T.; Ellis, Drummond; Loudon, J. D.

doi:10.1039/jr9490001074

Cited by 9 publications

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“…Acid catalyzed pyrolyses of amides, with the production of olefins, have also been observed (47a). For example, deaminocolchinol methyl ether (from N-acetylcolchinol methyl ether) and cyclohexene (from N-acetyl cyclohexylamine) have been obtained by Cook and co-workers by this acid catalyzed pyrolytic deamination (48).…”

Section: =Nmentioning

confidence: 99%

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Aliphatic deaminations in organic synthesis

Baumgarten¹

1966

J. Chem. Educ.

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Section: =Nmentioning

confidence: 99%

“…In particular, Bachmann, Cava, and Dreiding have found ( 70) that (-butyl hypochlorite converts certain primary amines to the corresponding ketone or aldehyde in 39-98% yields via the X-chloramine and iminc intermediates [eqn. (48)]. Photochemical Oxidation (Aldehyde and Ketone Formation).…”

Section: Rcqqh)mentioning

confidence: 99%

Aliphatic deaminations in organic synthesis

Baumgarten¹

1966

J. Chem. Educ.

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ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

DeTar

2011

Organic Reactions

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In the middle 1890s, three groups of chemists independently discovered a new cyclization reaction of certain appropriately constituted diazonium salts. Fischer and Schmidt reported that an aqueous solution of 2‐benzylbenzenediazonium chloride furnished fluorene on heating. Graebe and Ullman reported that 2‐benzoylbenzenediazonium chloride yielded fluorenone and Staedel reported a somewhat similar result from the action of nitrous acid on 2,2'‐diaminbenozpehnone, a reaction that produced a little 1‐hydroxyfluorenone. Two years later, Robert Pschorr applied the ring closure reaction to the diazonium salt derived from trans‐2‐amino‐alpha‐phenylcinnamic acid to obtain phenanthrene‐9‐carboxylic acid. The principal utility of these cyclizations reactions has been the synthesis of substituted ring structures in which the positions of the substituents are known.

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Olefins from Amines: TheHofmann Elimination Reaction and Amine Oxide Pyrolysis

Cope

Trumbull

2011

Organic Reactions

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The conversion of an amine to an olefin by elimination of the nitrogen atom and an adjoining hydrogen atom is a useful procedure for degradation and synthesis. The Hofmann exhaustive methylation method has been used most often to bring about change, but other methods as the thermal decomposition of amine oxides and the pyrolysis of amine phosphates or acetyl or benzoyl derivative have often been employed to advantage. This chapter reviews the Hofmann elimination because of its extensive history. Alternative methods are considered.

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229. Colchicine and related compounds. Part VII

Cited by 9 publications

References 0 publications

Aliphatic deaminations in organic synthesis

Aliphatic deaminations in organic synthesis

ThePschorr Synthesis and Related Diazonium Ring Closure Reactions

Olefins from Amines: TheHofmann Elimination Reaction and Amine Oxide Pyrolysis

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