Alcohols inversion of configuration

Phthalimides. Alcohols are activated by (Me2N=CHCl) CF toward displacement with potassium phthalimide. By this method the synthesis of chiral amines from secondary alcohols (inversion of configuration) is accessible. 

Alkyl Bromides from Aleohols. Alkyl bromides (29) are obtained in high yields by the reaction of the corresponding alcohols (28) with Me6Si2 and p)nidinium hydrobromide perbromide (eq 14). The substitution reaction is very fast for tertiary, allylic, and benzylic alcohols, but very slow for primary and secondary alcohols. Inversion of configuration is observed with secondary alcohols. 

N-Methyl-N,N -dicyclohexylcarbodiimidium iodide Iodides from alcohols Inversion of configuration... 

N,N-Diethyl-l,2,2-trichlorovinylamine is an effective reagent for the replacement of hydroxyl by chlorine. The yields are good in the cases of carboxylic acids, and prim., sec., and tert. alcohols. Inversion of configuration takes place with optically active compounds giving products of high optical purity. The reaction with amines yields amidines. F. e., also carboxylic acid chlorides, s. A. J. Speziale and R. C. Freeman, Am. Soc. 82, 909 (I960). 

---

See also in sourсe #XX -- [ ]

---