3-Chloroallylic alcohols

Soil Hydrolyzes in wet soil forming a5-3-chloroallyl alcohol (Castro and Belser, 1966). 

The Bjorksten organization was given a contract by the U.S. Air Force about 1949 (AFTR 6220) to explore the effect of glass fabric treatments on polyester laminate wet strength properties. A total of 2000 compounds were screened. The best of these, and still good by today s standards, was a nonaqueous solvent treatment (BJY) based on an equimolar adduct of vinyl trichlorosilane and /3-chloroallyl alcohol [3]. 

With mercuric salt catalysts, hydrogen chloride adds to give 2-chloroallyl alcohol, 2-chloroprop-2-en-l-ol [5976-47-6] (27). 

Maddy KT, Fong HR, Lowe JA, et al. 1982. A study of well water in selected California communities for residues of 1,3-dichloropropene, chloroallyl alcohol and 49 organophosphate or chlorinated hydrocarbon pesticides. Bull Environ Contam Toxicol 29 354-359. 

Even the reaction with 1,1-disubstituted allenes delivered 2-chloroallyl alcohols 16 with the hydroxyl group connected to the more substituted terminus [15]. 

Metabolic activation of 1,3-dichloropropene, as suggested by the use of specific inhibitors of metabolism in the Salmonella typhimurium gene mutation assay, proceeds via an hydrolytic-oxidative pathway the first step of which is hydrolysis to chloroallyl alcohol, which is then oxidized to chloroacrolein (Neudecker Henschler, 1986). 

The chlorofluorination of 2-fluoroallyl and 2-chloroallyl alcohols,allyl acetates,and... 

The chlorofluorination of 2-fluoroallyl and 2-chloroallyl alcohols,166 290 allyl acetates,256 and 1-substituted methyl (Z)-2-chloroacrylates241 with hexachloromelamine and hydrogen fluoride has been investigated (see Table 19). 

Attempts to use other hydroxymethyl monomers such as allyl alcohol, 2-methylallyl alcohol, and 2-chloroallyl alcohol for isomerizational copolymerizations with methyl acrylate gave mixed results due to the poor copolymerization rate constants of these olefins and the ability of acrylic radicals to abstract hydrogen atoms from allyl alcohols. 

Lithium aluminum hydride is another reagent which has been employed to cleave 3,3-dichloro-cxo-tricyclo[4.2.1.0 ]nonyl acetates, e.g. 44 and 48, with eventual formation of bicyclo[4.2.1]-nonanones. The initial products were 2-chloroallyl alcohols, but these were catalytically reduced and then oxidized to ketones with sodium dichromate. ... 

Chiral alkenyl and cycloalkenyl oxiranes are valuable intermediates in organic synthesis [38]. Their asymmetric synthesis has been accomplished by several methods, including the epoxidation of allyl alcohols in combination with an oxidation and olefination [39a], the epoxidation of dienes [39b,c], the chloroallylation of aldehydes in combination with a 1,2-elimination [39f-h], and the reaction of S-ylides with aldehydes [39i]. Although these methods are efficient for the synthesis of alkenyl oxiranes, they are not well suited for cycloalkenyl oxiranes of the 56 type (Scheme 1.3.21). Therefore we had developed an interest in the asymmetric synthesis of the cycloalkenyl oxiranes 56 from the sulfonimidoyl-substituted homoallyl alcohols 7. It was speculated that the allylic sulfoximine group of 7 could be stereoselectively replaced by a Cl atom with formation of corresponding chlorohydrins 55 which upon base treatment should give the cycloalkenyl oxiranes 56. The feasibility of a Cl substitution of the sulfoximine group had been shown previously in the case of S-alkyl sulfoximines [40]. 

Further investigation of the equilibrium between titanacyclobutene and titanium vinyl alkylidene complexes, as discussed in Section 2.12.6.1.4, was reported recently <2007CEJ4074>, along with the incorporation of this reactivity pattern into the synthesis of conjugated dienes, homoallylic alcohols, vinylcyclopropanes, and phosphacyclobutenes from y-chloroallyl sulfides and a source of titanocene(ll). 

Q -(Trialkylstannyl) ether, obtained from the stannylation of a-chloroallyl ether by Bu3SnLi, allowed the stereoselective synthesis of lithioether and then, after Wittig rearrangement, the corresponding alcohol (Scheme 49) . ... 

Oda, Y. Matsuo, S. Saiko, K. (1992) An efficient synthesis of 3-chlorohomoallyl alcohols. Zinc-promoted 2-chloroallylation of carbonyl compounds with 2,3-dichloropropene in an aqueous solvent system. Tetrahedron Lett., 33,97-100. 

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