Ozonolysis of trans-2,3-dichloro-2-butene. Isolation of .alpha.-chloro peroxides

Griesbaum, Karl; Hofmann, Peter

doi:10.1021/ja00426a034

Cited by 49 publications

(15 citation statements)

References 7 publications

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“…Considerable evidence has been accrued in recent years for a Criegee-type cleavage pattern during the ozonolysis of substituted 1,2-dichloroethylenes in nonparticipating solvents (3)(4)(5). In a preliminary rationalization we have, therefore.…”

Section: Reaction Coursementioning

confidence: 91%

Ozonolysis of substituted 1,2-dichloroethylenes in methanol: products and reaction course

Huh¹,

Neumeister²,

Griesbaum³

1981

Can. J. Chem.

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TAE-SEONG HUH, JOACHIM NEUMEISTER, and KARL GRIESBAUM. Can. J. Chem. 59. 3188 (1981) Ozonolysis of trrins-2,3-dichloro-2-butene (5a). of trans-3.4-dichloro-3-hexene (5b), and of 1.2-dichlorocyclohexene in methanol and in solutions of sodium methoxide in methanol have been examined. They afforded in high yields the corresponding ester fragments methyl acetate (6a). methyl propionate (6b), and dimethyl adipate (a), respectively. By trapping with phenylacetylene and formation of 1.1-dichloro-2.2-dimethoxy-2-phenylethan the presence of methyl hypochlorite in the ozonolysis products was cstablishcd. A rcaction course has been proposed which is in accord with these results.

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Section: Reaction Coursementioning

confidence: 91%

Ozonolysis of substituted 1,2-dichloroethylenes in methanol: products and reaction course

Huh¹,

Neumeister²,

Griesbaum³

1981

Can. J. Chem.

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“…Der cyclische Perester 9, der die Strukturmerkmale von 6 besitzt, entsteht bei der Ozonolyse von 1,2-Dichloracenaphthylen in inerten Lljsungsmitteln und wurde fruher irrtllmlich als 6b,9a-Dichlor-6b,9a-dihydroacenaphtho[l,2-d] [ 1,2,3] trioxol beschrie-ben8). Die thermisch instabile Verbindung wurde durch Chromatographie an Kieselgel mit einer gekuhlten S u l e in l0proz.…”

Section: Peresterdarstellungunclassified

Darstellung von Percarbonsäure‐1,1‐dichloralkylestern

et al. 1985

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1 ,I-Dichlorethylhydroperoxid (4a) und 1 ,I-Dichlorpropylhydroperoxid (4 b) reagieren mit einer Reihe von Saurechloriden zu den Percarbonsaure-1 ,1-dichloralkylestern 6aq. Die Hydrolyseempfindlichkeit und thermische Instabilitat von 4 sowie der leichte Zerfall einiger Perester fuhren zu Nebenprodukten. In manchen Fallen gelingt die Darstellung von 6 ohne die Isolierung des Hydroperoxids 4. So werden die Perester 6c und e in zufriedenstellender Ausbeute erhalten, wenn die Ozonbehandlung von 2,3-Dichlor-2-buten (1 a) in tiberschtissigem Propionyl-bzw. Butyrylchlorid erfolgt. Bei der Darstellung von 6a durch Ozonolyse von 1 a in Gegenwart von Tetraalkylammoniumchlorid wird das 1 ,I-Dichlorethylperoxid-Ion (7) als Zwischenstufe angenommen. Preparation of I,]-Dichloroalkyl Percarboxylates1,l-Dichloroethyl hydroperoxide (4a) and 1 ,I-dichloropropyl hydroperoxide (4b) react with a number of acyl chlorides to yield the 1,l-dichloroalkyl percarboxylates 6aq. The sensitivity of 4 to hydrolysis and thermal decomposition as well as the ready decomposition of some of the peresters lead to by-products. In certain cases the prepmation of 6 does not require the isolation of the hydroperoxide 4. Thus, 6 e and e are produced in satisfactory yields when ozonolysis of 2,3-dichloro-2-butene (la) is carried out in excess propionyl or butyryl chloride. The 1,l-dichloroethyl peroxide ion (7) is presumed to be the intermediate in the ozonolysis of l a in the presence of tetraalkylammonium chloride.Percarbonsaureester konnen allgemein durch Umsetzung von Hydroperoxiden mit Carbonsauren bzw. Carbonsaurechloriden dargestellt werden. Sehr schonend verlauft die Veresterung mit Siurechloriden in Pyridinlosung I). Als Ausgangsverbindungen zur Darstellung von Percarbon-Chem.

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“…Peroxide 3 has been prepared by Schulz, Kirschke, and Hçhne via bis(1,3-dichlorohydroperoxypropan-2-yl)peroxide by the reaction of 1,3-dichloroacetone with hydrogen peroxide in an acidic environment followed by the action of lead(IV) acetate [4]. Preparation of 3 by ozonolysis of 2,3-dichloro-2-butene has been published by Griesbaum and Hofmann [5].…”

Section: Introductionmentioning

confidence: 99%

Study of TATP: Formation of New Chloroderivates of Triacetone Triperoxide

Matyáš

Jirásko

Lyčka

et al. 2011

Propellants Explo Pyrotec

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The existence of two new types of chloroderivates of cyclic acetone peroxides -3-(chloromethyl)-3,6,6,9,9-pentamethyl-1,2,4,5,7,8-hexoxonane and 3,6-bis(chloromethyl)-3,6,9,9-tetramethyl-1,2,4,5,7,8-hexoxonane was proved by HPLC/MS/MS and NMR in the reaction products when acetone and hydrogen peroxide are mixed in the presence of excess hydrochloric acid (molar ratio hydrochloric acid to acetone n c /n a = 2.5). The details of analysis, and the conditions under which these asymmetric chloroderivates of cyclic peroxides form, are described.

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Ozonolysis of trans-2,3-dichloro-2-butene. Isolation of .alpha.-chloro peroxides

Cited by 49 publications

References 7 publications

Ozonolysis of substituted 1,2-dichloroethylenes in methanol: products and reaction course

Ozonolysis of substituted 1,2-dichloroethylenes in methanol: products and reaction course

Darstellung von Percarbonsäure‐1,1‐dichloralkylestern

Study of TATP: Formation of New Chloroderivates of Triacetone Triperoxide

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