Dimethyldioxirane

Structural formula
General
Surname	Dimethyldioxirane
other names	DMDO; DDO; 3,3-dimethyldioxirane;
Molecular formula	C 3 H 6 O 2
External identifiers / databases
PubChem	115197
Wikidata	Q762482
properties
Molar mass	74.08 g mol −1
solubility	soluble in acetone and dichloromethane ; soluble in most organic solvents ;
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethyldioxirane is a chemical compound from the group of dioxiranes , which is only known in dilute solution.

Extraction and presentation

Dimethyldioxirane can be obtained by reacting acetone with a neutral buffered solution of potassium peroxomonosulfate (trade names including Oxone and Caroat).

properties

Dimethyldioxirane is a chemical compound known only in dilute solution, which is soluble in most organic solvents , but reacts slowly with many of them. At −10 to −20 ° C, the solution can be stored for about a week in the absence of light and without contact to traces of heavy metals.

use

Dimethyldioxirane is used as a selective, reactive oxidizing reagent for the epoxidation of alkenes and arenes , for the oxidation of alcohols , ethers , amines , imines and sulfides and for the production of aromatic nitro compounds.

proof

The concentration of the compound can be determined by iodometric titration .

Individual evidence

↑ ^a ^b ^c ^d ^e J. K. Crandall, R. Curc, L. D'Accolti, C. Fusco: Dimethyldioxirane . e-EROS Encyclopedia of Reagents for Organic Synthesis, 2005, doi : 10.1002 / 047084289X.rd329.pub2 .
↑ Tomislav Rovis: Handbook of Reagents for Organic Synthesis Reagents for Organocatalysis . John Wiley & Sons, 2016, ISBN 978-1-119-06101-4 , pp. 320 ( limited preview in Google Book search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Bansal: Organic Reaction Mechanisms . Tata McGraw-Hill Education, 1998, ISBN 978-0-07-462083-0 ( limited preview in Google Book Search).
↑ Waldemar Adam: Oxidation of Organic Compounds by Dioxiranes . John Wiley & Sons, 2009, ISBN 978-0-470-45407-7 , pp. 669 ( limited preview in Google Book search).
↑ Jai Prakash Agrawal, Robert Hodgson: Organic Chemistry of Explosives . John Wiley & Sons, 2007, ISBN 0-470-05935-4 , pp. 155 ( limited preview in Google Book search).

[eros-1] J. K. Crandall, R. Curc, L. D'Accolti, C. Fusco: Dimethyldioxirane . e-EROS Encyclopedia of Reagents for Organic Synthesis, 2005, doi : 10.1002 / 047084289X.rd329.pub2 .

[Tomislav_Rovis-2] Tomislav Rovis: Handbook of Reagents for Organic Synthesis Reagents for Organocatalysis . John Wiley & Sons, 2016, ISBN 978-1-119-06101-4 , pp. 320 ( limited preview in Google Book search).

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Bansal-4] Bansal: Organic Reaction Mechanisms . Tata McGraw-Hill Education, 1998, ISBN 978-0-07-462083-0 ( limited preview in Google Book Search).

[Waldemar_Adam-5] Waldemar Adam: Oxidation of Organic Compounds by Dioxiranes . John Wiley & Sons, 2009, ISBN 978-0-470-45407-7 , pp. 669 ( limited preview in Google Book search).

[Jai_Prakash_Agrawal,_Robert_Hodgson-6] Jai Prakash Agrawal, Robert Hodgson: Organic Chemistry of Explosives . John Wiley & Sons, 2007, ISBN 0-470-05935-4 , pp. 155 ( limited preview in Google Book search).