1,2-Dioxolane

vanc 1,2-dioxolane.svg skin-invert 120px 1,2-Dioxolane 1,2-Dioxacyclopentane correct chemspider 121835 DTXSID10195890 correct chemspider 1S/C3H6O2/c1-2-4-5-3-1/h1-3H2 correct chemspider SNQXJPARXFUULZ-UHFFFAOYSA-N correct CAS 4362-13-4 138198 C1COOC1 3 6 2 1,2-Dioxolane is a chemical compound with formula C3H6O2, consisting of a ring of three carbon atoms and two oxygen atoms in adjacent positions. Its condensed structural formula is [–(CH 2)3–O–O–]. The compound is an organic peroxide, specifically an endoperoxide, and a structural isomer of the much more common 1,3-dioxolane, which is often called simply "dioxolane". Synthesis Synthesis methods for the 1,2-dioxolane core structure include oxidation of cyclopropane derivatives with singlet oxygen or molecular oxygen with a suitable catalyst, the use of autooxidation, nucleophilic displacement with hydrogen peroxide, treatment with mercury(II) nitrate, photolysis of extended π-systems, reaction of a bis-silylperoxide and an alkene, or reaction with a 2-perhydroxy 4-alkene with diethylamine or mercury(II) acetate. Occurrence Some derivatives occur naturally, for example in Calophyllum dispar and from the seeds of the mamey (Mammea americana). Plakinic acid A (3,5-peroxy 3Z,5Z,7,11-tetramethyl 13-phenyl-8E,12E-tridecadienoic acid) and similar compounds were isolated from sponges of the Plakortis genus. Nardosinone is a sesquiterpene derivative with a 1,2-dioxolane element isolated from the plant Adenosma caeruleum. Uses Synthetic and natural dioxolane derivatives have been used or considered as antimalarial drugs. Plakinic acid A and related compounds showed antifungal action. See also 1,2-Dioxane 1,2-Dioxetane 1,2-Dithiolane References Helesbeux JJ, Peyronnet D, Labaïed M, Grellier P, Frappier F, Seraphin D, Richomme P, Duval O 6 Synthesis and antimalarial activity of some new 1,2-dioxolane derivatives Journal of Enzyme Inhibition and Medicinal Chemistry 17 6 431–7 December 2002 12683680 10.1080/1475636021000005677 41059563 Martyn DC, Ramirez AP, Beattie MJ, Cortese JF, Patel V, Rush MA, Woerpel KA, Clardy J 6 Synthesis of spiro-1,2-dioxolanes and their activity against Plasmodium falciparum Bioorganic & Medicinal Chemistry Letters 18 24 6521–4 December 2008 18993067 10.1016/j.bmcl.2008.10.083 Akasaka T, Fukuoka K, Ando W 10.1016/0040-4039(91)80568-Q Formation of 1,2-dioxolane in the singlet oxygenation of cyclopropane 1991 Tetrahedron Letters 32 52 7695–7698 Liu HH, Jin HX, Wu YK 10.1002/cjoc.20040220930 Synthesis and cleavage studies of a 1,2-dioxolane-type peroxide 2010 Chinese Journal of Chemistry 22 9 1029–1033 Mata S, González J, Vicente R, López LA 10.1002/ejoc.201600393 Zinc-Catalyzed Multicomponent Reactions: Easy Access to Furyl-Substituted Cyclopropane and 1,2-Dioxolane Derivatives 2016 European Journal of Organic Chemistry 2016 15 2681–2687 https://ria.asturias.es/RIA/bitstream/123456789/8188/1/Archivo.pdf Feldman KS, Simpson RE 10.1016/S0040-4039(01)93404-5 Stereochemical studies on the preparation and subsequent reductive cleavage of 1,2-dioxolanes. Application to the synthesis of (±)-yashabushitriol 1989 Tetrahedron Letters 30 50 6985–6988 Booldworth AJ, Tallant NA 10.1039/C39920000428 1,2,4-Trioxane versus 1,2-dioxolane formation in the mercury(II) acetate-mediated cyclisation of hemiperoxyacetals derived from allylic hydroperoxides 1992 Journal of the Chemical Society, Chemical Communications 5 428 Lay TH, Bozzelli JW 10.1016/S0009-2614(97)00168-1 Enthalpies of formation of cyclic alkyl peroxides: Dioxirane, 1,2-dioxetane, 1,2-dioxolane, and 1,2-dioxane 199 Chemical Physics Letters 268 1–2 175–179 1997CPL...268..175L Phillipson DW, Rinehart Jr K 10.1021/ja00364a045 Antifungal peroxide-containing acids from two Caribbean sponges 1983 Journal of the American Chemical Society 105 26 7735–7736 Dai P, Trullinger TK, Liu X, Dussault PH Asymmetric synthesis of 1,2-dioxolane-3-acetic acids: synthesis and configurational assignment of plakinic acid A The Journal of Organic Chemistry 71 6 2283–92 March 2006 16526775 10.1021/jo0522254 Bloodworth AJ, Bothwell BD, Collins AN, Maidwell NL 10.1016/0040-4039(96)00143-8 A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group A short synthesis of naturally occurring and other analogues of plakinic acids that contain the 1,2-dioxolane group 1996 Tetrahedron Letters 37 11 1885–1888 Kandur WV, Richert KJ, Rieder CJ, Thomas AM, Hu C, Ziller JW, Woerpel KA Synthesis and reactivity of 1,2-dioxolanes from β,γ-epoxy ketones Organic Letters 16 10 2650–3 May 2014 24779430 10.1021/ol500835f Demaison J 10.1007/10201404_40 2.5.2.5 Elements with two or three internal rotors Diamagnetic Molecules Landolt-Börnstein - Group II Molecules and Radicals 1982 14a 415–425 3-540-11365-7 Category:Oxygen heterocycles Category:Organic peroxides