NDLI: Preparation, reactions, and structure of 5,10-epoxy-, 5,10-epithio-, 5,10-episeleno-, and 5,10-epitelluro-5,10-dihydroarsanthren

Content Provider	Royal Society of Chemistry (RSC)
Author	Allen, David W. Mann, Frederick G. Watson, David G. Kennard, Olga Coppola, James C. Motherwell, William D. S.
Copyright Year	1970
Abstract	The compound recorded by Kalb (1921) as ‘arsanthren oxide’ has been more fully investigated. Its monomeric nature, now established, confirms that it is 5,10-epoxy-5,10-dihydroarsanthren. Its ready formation by hydrolysis of 5,10-dichloro-5,10-dihydroarsanthren with cold aqueous sodium carbonate presumably proceeds by the cyclisation of the intermediate 5-chloro-10-hydroxy- or 5,10-dihydroxy-compound. If the 5,10-dichloro- 5,10-dihydroarsanthren, like the 5,10-dimethyl analogue, has the folded ‘butterfly’ conformation, with the two substituents in the cis position, this process involves a flexing of the molecule about the As–As axis, which for steric reasons can be complete only when the two substituents react to form a five-membered ring.The 5,10-epoxy-compound is unaffected by boiling methyl iodide, but is readily oxidised to arsanthrenic acid and is converted by methylmagnesium iodide into 5,10-dihydro-5,10-dimethylarsanthren. In ethanol it reacts rapidly with hydrogen sulphide, selenide, and telluride, giving the crystalline 5,10-epithio-, 5,10-episeleno-, and 5,10-epitelluro-analogues. X-Ray crystal analysis has established the complete structure and conformation of the 5,10-epithio-compound, but although this compound and the episeleno- and epitelluro-compounds have closely related cell constants, they are not isomorphous.The u.v. i.r., n.m.r., and mass spectra of the four compounds are discussed. The mass spectral fragmentation patterns of various related arsanthren compounds are briefly recorded.
Starting Page	810
Ending Page	815
Page Count	6
File Format	PDF
ISSN	00224952
Volume Number	0
Issue Number	6
Journal	Journal of the Chemical Society C: Organic
DOI	10.1039/J39700000810
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Methyl iodide Butterfly Methylmagnesium chloride Chemical structure Alcohol Crystal Analysis Kalb Hydrolysis Hydrogen sulfide Carboxylic acid Epoxide Sodium carbonate Selenium
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry

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