α-Oximinoketones. V. The Synthesis of 5-Cyano-2-oximinovaleric Acid and DL-Lysine from 2,6-Dioximinocyclohexanone<sup>1</sup>

Ferris, Arthur F.; Gould, Francis E.; Latourette, Harold K.

doi:10.1021/jo01074a002

Cited by 15 publications

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“…An extended search ivas made in an effort to find a catalyst-solvent system which would permit hydrogenation of ethyl 5-cyano-2-oximinovalerate to lysine without the side reactions which apparently were responsible for the low yields obtained in earlier work. [3][4] In the course of this search the combination of Raney nickel and acetic anhydride was tried. Although Adkins' classic work on catalytic hydrogenation7 states that this combination cannot be used, recent work8-10 (6) O.…”

mentioning

confidence: 99%

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹

Ferris¹,

Gould²,

Stange³

1960

J. Org. Chem.

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confidence: 99%

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹

Ferris¹,

Gould²,

Stange³

1960

J. Org. Chem.

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TheBeckmann Reactions: Rearrangements, Elimination–Additions, Fragmentations, and Rearrangement–Cyclizations

Gawley

1988

Organic Reactions

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The Beckmann rearrangement, the acid‐mediated isomerization of oximes to amides, was discovered by Beckmann in 1886. As one of the oldest and most familiar transformations in organic chemistry, it has been reviewed several times. What has become known as the Beckmann fragmentation was in fact first observed by Wallach in 1889 but was not developed extensively until the 1960s. It has been referred to by several names over the years and has also been reviewed. The rearrangement cyclization is the intramolecular cyclization of a nitrilium ion generated by Beckmann rearrangement from an oxime. Within the context of an aromatic terminator, the process was first reported by Goldschmidt in 1895. Wallach reported the first case of an aliphatic terminator in 1901, although the reported structure was incorrect, and Perkin was apparently the first to observe a heteroatom terminator, but he also reported an incorrect structure. The process has been exploited only quite recently. This chapter is an update of these reactions, last reviewed in this series in 1960. Not covered are transformations that have been labeled Beckmann‐type reactions but are mechanistically unrelated. The most prominent of these is the so‐called photochemical Beckmann rearrangement, first observed by De Mayo in 1963 and discussed in a review several years ago. Worthy of mention, however, is the fact that many oximes that suffer fragmentation under acidic conditions undergo rearrangement when photolyzed. Throughout this chapter, the ( E ) and ( Z ) nomenclature is used to describe oxime geometry.

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Reduction of the cyano group

Rabinovitz

1970

PATAI'S Chemistry of Functional Groups

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α-Oximinoketones. V. The Synthesis of 5-Cyano-2-oximinovaleric Acid and DL-Lysine from 2,6-Dioximinocyclohexanone¹

Cited by 15 publications

References 1 publication

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹

TheBeckmann Reactions: Rearrangements, Elimination–Additions, Fragmentations, and Rearrangement–Cyclizations

Reduction of the cyano group

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α-Oximinoketones. V. The Synthesis of 5-Cyano-2-oximinovaleric Acid and DL-Lysine from 2,6-Dioximinocyclohexanone1

Cited by 15 publications

References 1 publication

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone1

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone1

TheBeckmann Reactions: Rearrangements, Elimination–Additions, Fragmentations, and Rearrangement–Cyclizations

Reduction of the cyano group

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α-Oximinoketones. V. The Synthesis of 5-Cyano-2-oximinovaleric Acid and DL-Lysine from 2,6-Dioximinocyclohexanone¹

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹

α-Oximinoketones. VII. Synthesis of Alkyl 5-Cyano-2-oximinovalerates and DL-Lysine from 2,6-Dioximinocyclohexanone¹