284-20-8Relevant academic research and scientific papers
Telomerization of Z,Z-cyclooctadiene with halomethanes catalyzed by chromium, copper, and molybdenum compounds in the presence of water
Khusnutdinov,Shchadneva,Oshnyakova,Dzhemilev
experimental part, p. 435 - 441 (2012/04/23)
The telomerization of 1Z,5Z-cyclooctadiene with halogenated methanes (CCl4, CBrCl3, CHCl3, CH2Cl 2) mediated by chromium, copper, and molybdenum complexes has been investigated. It has been shown that the use of water as a nucleophilic additive promotes the formation of 1,4- and 1,5-epoxycyclooctanes and anti-8-(trichloromethyl)bicyclo[3.2.1]octan-exo-2-ol. Pleiades Publishing, Ltd., 2011.
ORGANOTINS AS ETHERIFICATION CATALYSTS. III. ETHERIFICATIONS AND HYDRO-HYDROXY-ELIMINATIONS PROMOTED BY BUTYLTIN TRICHLORIDE
Marton, Daniele,Slaviero, Pierangelo,Tagliavini, Giuseppe
, p. 7099 - 7108 (2007/10/02)
Butyltin trichloride, as a catalyst precursor, promotes the following processes: (i) etherification of 2,3-unsaturated alcohols, (ii) etherification of functional diols, (iii) cyclization of 2,5-hexanedione, and (iv) dehydration of cyclic diols.Many examples are reported.
Photoinduced Transformations. 73. Transformations of Five- (and Six-) Membered Cyclic Alcohols into Five- (and Six-) Membered Cyclic Ethers - A New Method of a Two-Step Transformation of Hydroxy Steroids into Oxasteroids
Suginome, Hiroshi,Yamada, Shinji
, p. 3753 - 3762 (2007/10/02)
We set out to describe a two-step transformation of saturated hydroxy steroids into oxasteroids with an oxgen-containing ring of the same size as that of the starting ring.The irradiation of the hypoiodites generated in situ by means of the reaction of the hydroxy steroids with an excess of mercury(II)oxide and iodine gives novel formates arising from the successive reactions triggered by a β-scission of the corresponding alkoxy radical.These formates can readily be transformed into oxasteroids by a treatment with a complex metal hydride or methyllithium.The method is exemplified by the transformations of 1-, 3-, and 17-hydroxy steroids into the corresponding oxasteroids.Experiments in which we have used 18O labeled mercury(II)oxide as a source of I218O provide evidence that the oxygen atom in the oxasteroids is derived from the hydroxyl group of the starting alcohol and not from the oxygen of mercury(II)oxide.This suggests that the pathway of the formation of the formates involves (a) β-scission of the corresponding alkoxy radical to give a carbon centered radical intermediate with a carbonyl group, (b) its intramolecular combination with the carbonyl oxgen to form a tetrahydropyranyl radical or an oxepanyl radical, (c) its reaction with iodine oxide or *OI to generate a new hypoiodite, and (d) a regiospecific β-scission of the second alkoxy radical generated from it.
Oxymetallation. Part 13. Synthesis of Bicyclic Peroxides via Peroxymercuriation of Cyclic Dienes
Bloodworth, A.J.,Khan, Jamil A.,Loveitt, M.E.
, p. 621 - 632 (2007/10/02)
The bis-mercuriated derivative (12) of 9,10-dioxabicyclodecane has been prepared by peroxymercuriation of cis,cis-octa-1,5-diene, but substantial amounts of bicyclic ethers are also formed in the reaction.The bicyclic peroxides (4) and (5) have been obtained from (12) by reduction and brominolysis respectively. 8,9-Dioxabicyclodecane (6) and the dibromo-derivative (7) have similarly been prepared by peroxymercuriation and demercuriation of cyclo-octa-1,4-diene.It is suggested that the isomeric purity of the peroxides and the concurrent formation of bicyclic ethers both result from equilibrium control of reversible (per)oxymercuriation-de(per)oxymercuriation.A low yield of the -peroxide (8) has been obtained by peroxymercuriation and brominolysis of cyclohexa-1,4-diene, but attempts to prepare -compounds from 5,5-disubstituted cyclopentadienes have been unsuccessful.
