The possibility has been shown of synthesizing acetylenic derivatives of 1,4-dioxane in high yield by the interaction of glycidyl ethers of acetylenic alcohols with ethylene bromohydrin in the presence of boron trifluoride etherate. Dehydrobromination of the corresponding bromohydrin was then carried out in the presence of metallic sodium in absolute diethyl ether. Acetylenic derivatives of 1,4-dioxane enter into hydrosilylation, aminomethylation, and diene condensation reactions with the formation of new derivatives of 1,4-dioxane.It is known that oxygen-containing heterocyclic compounds with multiple bonds are reactive and may be applied widely in organic synthesis for obtaining polyfunctional compounds with practically useful properties, particularly biologically active compounds [1][2][3][4][5]. The preparation of unsaturated derivatives of 1,4-dioxane from glycidyl ethers of unsaturated alcohols has been insufficiently studied [5][6][7][8][9]. While continuing investigations started previously [10], we have synthesized a series of acetylenic derivatives of 1,4-dioxane from glycidyl ethers of primary and tertiary acetylenic alcohols and have studied some of their chemical conversions. OH Br O O O R R O O R O O H Br R O O R O R O + ( ) n BF 3· · OEt 2 ( ) n ( ) n 1a -d Na ether 1 a, c R = H, b, d R = Me; a, b n = 0, c, d n = 1
A study was made of the interaction of thiourea with saturated and unsaturated organosilicon oxiranes in absolute methyl alcohol in a medium of potassium hydroxide, and methods were developed for the synthesis of unsaturated and unsaturated organosilicon silicides with a yield of 65–75%.The studies carried out revealed that the synthesized organosilicon episulfides are very reactive compounds and can react with nucleophilic and electrophilic reagents, while forming the corresponding silicon derivatives. The IR- spectra of the products were studied. It should be noted that, when comparing the IR- spectra of oxiranes and episulfides, it was revealed that the stretching vibrations of the CH2 group of the episulfide ring are underestimated by 50–70 cm-1 in comparison with the oxirane ring
Synthesis and Properties of Halogen-Containing Allyl Series Epoxy-Compounds. -Reaction of allylic alcohol (I) with epichlorohydrin provides access to epoxide (III) containing a 2-haloallyl substituent. On reaction with KOH, dehydrohalogenation proceeds at the allylic residue to furnish an epoxide containing an tethered ethynyl residue (VII), while the reactions with amine (IV) and thiourea take place at the epoxide ring. A second synthetic access to halogen-substituted allylepoxides [e.g. (X)] is presented, involving the reaction of α,β-dihaloaldehyde (VIII) with allylmagnesium bromide. -(VELIYEV, M. G.; SHATIROVA, M. I.; ASKEROV, O. V.; GAKHRAMANOV, R. F.; Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. 44 (2001) 1, 59-62; Inst. polimer. mater. Akad. nauk Azerb., Sumgait 373204, Azerbaijan; RU)
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