Allyl ethyl sulfide

Thioacetaldehyde. Maier and coworkers obtained this compound by flash pyrolysis of allyl ethyl sulfide in an argon matrix182. Its IR spectrum does not show a characteristic C=S stretching band. A comparison of the observed spectrum with the calculated one [the MP2/6-31G(d) level] allowed the identification of the molecule and further showed the extensive coupling between the normal C=S stretching mode and other normal modes. 

Ethyl vinyl sulfide Isopropyl methyl sulfide Methyl n-propyl sulfide leri-Butyl methyl sulfide Chloromethyl methyl sulfide Ethyl isopropyl sulfide Isobutyl methyl sulfide Methyl 2-methylallyl sulfide Allyl ethyl sulfide Ethyl n-propyl sulfide... 

Methyl vinyl sulfide Divinyl sulfide (Vinyl sulfide) Allyl methyl sulfide Diethyl sulfide (Ethyl sulfide)... 

Isopropyl propyl sulfide ser-Butyl ethyl sulfide Ethyl isobntyl sulfide Diallyl sulfide (Allyl sulfide)... 

Notes and discussion. This reaction can be utilized for the preparation of a-allyl, ethyl, phenyl and substituted aryl thioglycosides of sialic acid. NMR and NMR spectra of the crude reaction mixtures have confirmed that complete anomeric inversion occurs under the PTC condition. Adoption of tetrabutylammoniumhydro-gen sulfide as a PTC is critical for mild reaction conditions, otherwise, if triethylbenzylammonium chloride is employed, more harsh conditions are required. The use of ethyl acetate is advantageous over dichloromethane owing to the production of PhSCH2Cl and (PhS)2CH2 resulting from nucleophilic displacement of one or two chlorides of dichloromethane with thiophenol in the model experiment. 

The chemistry and procedures for modification of the - CO2H groups of PAA hyperbranched grafts on PE powder were analogous to those used for PAA grafts on PE or PP films and wafers. For example, a 90% yield in ester formation was possible using acid-catalyzed Fisher esterification. Likewise, quantitative reduction (ethyl chloroformate activation, borane-dimethyl sulfide reduction) to hyperbranched poly(allyl alcohol)s and amidation all could be carried out using procedures like those used for PAA/Au surfaces. 

Sulfide, ethyl iso-propyl Rh Sulfide, methyl allyl Rh ... 

Oxidation of ethyl 7-allyl-10-methoxy-4-oxo-6,7-dihydro-4//-pyrimido-[2,l-a]isoquinoline-3-carboxylate (99) by ozone in methylene chloride at -70°C, then treatment of the mixture with dimethyl sulfide at ambient temperature for 1 h gave either 7-(2-oxoethyl)- or 7-(2,2-dimethoxyethyl) derivatives (105 and 106), depending upon whether methanol was used during the workup (78USP4127720). 

Direct allylation of rhodanine 49 (Scheme 13) under Pd(0)-catalysis with cinnamyl ethyl carbonate affords the /V-allylated compound 50. However, allylation with cinnamyl bromide and a base is not regioselective, producing a mixture of 50 and sulfide 51. Sulfide 51 isomerizes to 50 under palladium catalysis (N > S), thus indicating that Pd(0)-catalyzed allylation of 49 is thermodynamically controlled (93T1465). 

This overriding effect of 1,3-chirality transfer as compared to induced diastereoselectivity was also observed in chiral, nonracemic, secondary allylic sulfides bearing a remote chiral dioxolanyl moiety (Scheme 91) [215]. The reactions of E-(S)-570 and Z- R)-571 with ethyl diazoacetate under the influence of various Rh catalysts delivered ylides which rearranged to products 372 and 2 -epi-372. From the analysis of the products it was deduced that 1,3-chirality was almost complete, whereas the stereochemical outcome at C2 differed somewhat with the catalysts used and was only modest in all cases. Obviously the reaction of 370 to the major diastereomer epz-372 involves TS-I or TS-II (Scheme 88) (R = dioxolanyl moiety, R = Me, G = C02Et) with the absolute topicity of attack being Re (C2 )ISi (C3). After desulfanylation only... 

Thiazol-2-yl allyl sulfides react with organomagnesium compounds in the presence of CuBr to afford optically active alkenes in good yields and selectivities <1996T10799>. Thiazole and benzothiazole allyl sulfides have been shown to react with excess ethyl diazoacetate in the presence of a copper(i) hexafluorophosphate acetonitrile complex to give, via formation of the resultant homoallylic sulfide intermediates, conjugated dienoic esters in good yields <1997TL3289>. /3-Ketosulfides of benzothiazole 143 are very prone to deprotonation by weak bases. Treatment... 

The lithiation of ethyl allyl sulfide followed by transmetallation with titanium isopropoxide engenders an allyltitanium reagent formulated as (26 Scheme 8). This and related reagents add to aldehydes or ketones to afford hydroxy sulfides, which are converted to epoxides as shown. The power of this method for the stereoselective generation of even trisubstituted epoxides is evident from Scheme 8 and equation (18). Reagent (26a), prepared as shown in Scheme 8a, undergoes addition to ketone (26b) to afford product exclusively resulting from chelation-controlled diastereofacial addition (as a mixture of epimers at the position shown). ... 

Doyle has shown that the rhodium-catalyzed reaction of allylic sulfides and amines with ethyl diazoacetate produced smoothly the products of 3,2-rearrangement. In contrast with the copper-catalyzed reaction, allylic amines can be used and the yields are good to high (Scheme 44) virtually no cyclopro-panation is observed. These observations demonstrate the superiority of rhodium catalysts compared with either copper ones or the use of light. 

Carbenoid attack at the heteroatom of allylic halides, ethers, amines, sulfides, and selenides generates an allylic ylide 23 that can undergo [2,3] sigmatropic rearrangement and, less frequently, [1,2] insertion (C-X insertion with and without allylic rearrangement, respectively). Similarly, an Af-acyl-2,5-dihydropyrrole could be cyclopropanated with ethyl diazoacetate in good yield. 

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