Ethers => alkenes

Ether Alkene Ether Alkene Ether Alkene... 

Epoxides are regio- and stereoselectively transformed into fluorohydrins by silicon tetrafluoride m the presence of a Lewis base, such as diisopropyleth-ylamme and, m certain instances, water or tetrabutylammonium fluoride The reactions proceed under very mild conditions (0 to 20 C in 1,2-diohloroethane or diethyl ether) and are highly chemoselective alkenes, ethers, long-chain internal oxiranes, and carbon-silicon bonds remain intact The stereochemical outcome of the epoxide ring opening with silicon tetrafluoride depends on an additive used, without addition of water or a quaternary ammonium fluoride, as fluorohydrins are formed, whereas m the presence of these additives, only anti opening leading to trans isomers is observed [17, 18] (Table 2)... 

Alkyl Fluoride Alkene Ether Phos- phonaie... 

Nonfluorinated a- and P diketoms give the corresponding tetrafluoroalkanes as the major products together with considerable amounts of alkenes, ethers, and sulfites Formation of side products is reduced, and yields of tetrafluoroalkanes are greatly improved by conducting the lluori nation reactions in an excess of anhydrous hydrogen fluoride [176, 177]... 

Colby J, DI Stirling, H Dalton (1977) The soluble methane mono-oxygenase of Methylococcus capsulatus (Bath). Its ability to oxygenate -alkanes, -alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. Biochem J 165 395-401. 

Grignard reagents are quite restricted in the types of functional groups that can be present in either the organometallic or the carbonyl compound. Alkene, ether, and acetal functionality usually causes no difficulty but unprotected OH, NH, SH, or carbonyl groups cannot be present and CN and NOz groups cause problems in many cases. 

Fluoroalkane RF Isomerized Fluoroalkane Alkene Ether ROR Fluorophosphonate PhP(0)FOR... 

I) H2C=CHCH2OH (2) CH3CH=CHOH (3) CH3CH2CH2CH=0 (4) CH3OCH=CH2 alkene alcohols(enols) an aldehyde an alkene ether... 

Models showed that cyclization of the alkene ether adduct was sterically impossible. Cyclization after addition of the second monomeric unit is possible but apparently cannot compete with propagation. Cyclization to ring sizes greater than nine becomes progressively less favourable. 

Serebrennikova et al. reported that the detosylation of 189 with DBU afforded a pure cis-alkene ether (190) (69ZOR676). 

Alkoxylation may be achieved by anodic oxidation in an alcohol, often methanol (MeOH), containing a suitable electrolyte, such as KOH, NaOMe, NaCN, NaBp4, or NH4NO3 [9-12,31,32]. Substrates that have been alkoxylated in this manner include aromatic compounds (both nuclear and side-chain alkoxylation has been observed), alkenes, ethers including vinyl ethers, enamines, N, AA-dialkylamines, AA-alkylsubstituted amides, and A-alkylsubstituted carbamates. In many cases alkoxylation by substitution is a side reaction only to concurrent alkoxylation by addition [7,9,11,33]. 

Alkoxysulfonium salt 30, R=cyclohexyl, is isolable and has been fully characterized [73]. Decomposition of these salts in acetonitrile leads to alkenes, ethers, and AT-alkylacetamides. Notably absent from this list of decomposition products are aldehydes and ketones which are typically formed by the decomposition of alkoxysulfonium salts 31 derived from dimethylsulfoxide [74,75]. The lack of formation of aldehydes and ketones from 30 is consistent with the known mechanism [76-78], shown in Eq. (21), for formation of these compounds from 31 ... 

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