THE REACTION OF CYANOGEN WITH ORGANIC COMPOUNDS. VII. GRIGNARD REAGENTS<sup>1</sup>

Woodburn, Henry M.; Lathroum, Leo B.

doi:10.1021/jo01368a001

Cited by 11 publications

(3 citation statements)

References 3 publications

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“…The iminium intermediate can be deprotonated to the enamine9 or hydrolyzed to the corresponding carbonyl compound 5c. 10 Thus, deprotonated α‐aminonitriles also represent synthetic equivalents of acyl anions11 and can be used for the synthesis of 1,4‐dicarbonyl compounds,6b, 12 which may, for example, serve as precursors for furans, thiophenes, or pyrroles,13 as well as for stereoselective nucleophilic acylations 12c. 14…”

Section: Introductionmentioning

confidence: 99%

Heterocycles from α‐Aminonitriles

Otto

Opatz

2014

Chemistry A European J

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Owing to their various modes of reactivity, α-aminonitriles represent versatile building blocks for the construction of a wide range of nitrogen heterocycles. The present Concept article focuses on synthetic methodologies using their bifunctional nature which is the basis of their reactivity as α-amino carbanions and as iminium ions. Reactions exclusively taking place on either the amine or on the nitrile moiety will not be considered.

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Section: Introductionmentioning

confidence: 99%

Heterocycles from α‐Aminonitriles

Otto

Opatz

2014

Chemistry A European J

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“…[26][27][28] Enamines are accessible by dehydrocy-anation [29][30][31] and various methods for the reversal of the Strecker reaction have been described, normally converting a-aminonitriles back into their parent carbonyl compounds (Scheme 1). [32][33][34][35][36][37][38]…”

Section: Introductionmentioning

confidence: 99%

The Chemistry of Deprotonated α-Aminonitriles

Opatz¹

2009

Synthesis

104

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This review highlights various aspects of the chemistry of the anions of a-aminonitriles. Their structural features and their characteristic reactivity are discussed, along with various methods for their preparation. Special emphasis is given to synthetic applications of deprotonated a-aminonitriles which have been used as valuable and readily accessible synthetic equivalents of acyl anions and a-aminocarbanions.

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“…In THE investigation of the reactions of cyanogen with organic compounds (5)(6)(7)(8)(9)(10)(11), it was often found useful or necessary to convert the product into a derivative which could be stored for long periods of time without deterioration. Recently, references have been made to the utilization of oxamidines and oxalimidates in syntheses or analytical processes (1)(2)(3)(4).…”

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confidence: 99%