VII. THE CONDENSATION OF ARYL DIAZONIUM SALTS AND/OR HYDROXIDES WITH SECONDARY NITRO ALKANES<sup>1</sup>

Feasley, C. F.; Degering, Ed. F.

doi:10.1021/jo01189a004

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1950

2011

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“…The coupling of nitroparaffins with diazonium salts has been reviewed by Hass and Riley (1) and more recently has been described by Feasley and Degering (2) and by Nygaard, McCracken, and Hamilton (3). The present report deals with similar condensations using the aliphatic nitrosulfonates (4) in place of the nitroparaffins.…”

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The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

Gold¹,

Levine²

1951

J. Org. Chem.

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“…Present Address: Aerojet Engineering Corp., Azusa, California 2. Present Address: Norwalk,Connecticut.…”

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The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

Gold¹,

Levine²

1951

J. Org. Chem.

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The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Parmerter

2011

Organic Reactions

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A diazonium salt will couple with an aliphatic compound containing an activated carbon‐hydrogen bond. This discussion is limited to those reactions in which both the nitrogen atoms of the diazonium salts are retained in the resulting molecule. The discussion is further limited by the exclusion of coupling reactions, which occur with the elimination of a group from an activated methinyl compound, the Japp‐Klingemann reaction. These reactions are discussed in Chapter 2. Much of the early work with coupling was prompted by the desire to determine whether the products were of the azo or hydrazonestructure. It is difficult to establish the structures in such cases where the tautomeric forms are possible. It is generally considered that the hydrazone is the stable form.

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Chemie und Technologie der Nitroalkane

Schickh

1950

Angewandte Chemie

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h e r e Methoden zur Darstellung von NitroalkanenDas erste beschriebene Nitroalkan ist m. W. das 1 . 2 -D i n it r o a t h a n , das A. Semenow 1864l) durch Urnsetzung von Athylen rnit offenbar reinem Stickstofftetroxyd erhalten hat. 1872 wurden zwei Methoden zur Darstellung von Nitroalkanen beschrieben: Die von V . Meyer und 0. Stuber2), die in der Umsetzung von Alkyljodiden mit Silbernitrit besteht, wobei neben den Nitroverbindungen auch die Alkylnitrite entstehen, die durch die bedeutende Siedeptinktsdifferenz leicht zu trennen sind.

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VII. THE CONDENSATION OF ARYL DIAZONIUM SALTS AND/OR HYDROXIDES WITH SECONDARY NITRO ALKANES¹

Cited by 4 publications

References 6 publications

The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Chemie und Technologie der Nitroalkane

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VII. THE CONDENSATION OF ARYL DIAZONIUM SALTS AND/OR HYDROXIDES WITH SECONDARY NITRO ALKANES1

Cited by 4 publications

References 6 publications

The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

The Chemistry of Aliphatic Nitrosulfonates. IV. Coupling with Diazonium Salts

The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

Chemie und Technologie der Nitroalkane

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VII. THE CONDENSATION OF ARYL DIAZONIUM SALTS AND/OR HYDROXIDES WITH SECONDARY NITRO ALKANES¹