MECHANISM OF BENZIDINE AND SEMIDINE REARRANGEMENTS. PART XI. NOTES ON TWO TYPES OF DIAZO-REDUCTION

Journal Article · Sat Sep 01 04:00:00 EDT 1962 · Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc.

DOI:https://doi.org/10.1039/jr9620003314· OSTI ID:4777922

Banthorpe, D V; Hughes, E D

When the 1-nitronaphthalene-2-diazonium ion is reduced with protium-free D/sub 3/PO/sub 2/ in the presence of D/sub2/S0/sub 4/ in dioxa n, with exclusion of atmospheric moisture, most of the diazogroup is replaced by protium. This protium is derived from the dioxan, in which it becomes replaced by deuterium. A similar effect on deuteration through Grignard reagents and D/sub 2/O in ether is recalled, and an explanation is advanced which relates both effects to the autoxidation of ethers. when naphthalene-1-diazonium ions containing deuterium in known positions are converted by reductive coupling with buffered sulphite into 1,1'-azonaphthalenes, the original orientations of deuterium relative to nitrogen are preserved in both aryl groups of the azo-derivative. The deuterium orientations were determined in the corresponding hydrazocompounds, by rearranging them with acid, separating the products, and comparing the deuteritm contents of the factors and separated products. The results delimit possible views of the mechanism of the reductive coupling. lt is shown or confirmed that the various deuterated hydrazocompounds, the preparation and reactions of which are described in Parts IX and X, have the constitutions there assigned to them. (auth)

• Research Organization: University Coll., London
• NSA Number: NSA-16-032991
• OSTI ID: 4777922
• Journal Information: Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc., Journal Name: Journal of the Chemical Society (England) Divided into J. Chem. Soc. A, J. Chem. Soc. B, etc.; ISSN JCSOA
• Country of Publication: Country unknown/Code not available
• Language: English

Related Subjects

CHEMISTRY
CONFIGURATION
COUPLING
DEUTERIUM COMPOUNDS
DIOXANE
GRIGNARD REAGENTS
HEAVY WATER
HUMIDITY
HYDROGEN
INTERACTIONS
ORGANIC NITROGEN COMPOUNDS
ORGANOMETALLICS
OXIDATION
PHOSPHORIC ACID
PREPARATION
REACTION KINETICS
REDUCTION
SOLVENTS
SULFURIC ACID