Reductive Telluration of Aliphatic Aldehydes with Hydrogen Telluride. A New Synthesis of Dialkyl Ditellurides

Abstract

Reaction of aliphatic aldehydes with hydrogen telluride under acidic conditions gave dialkyl ditellurides in moderate yields. The use of deuterium telluride formed in situ from aluminum telluride and deuterium oxide provided a facile synthetic method of 1,1′-dideuterated dialkyl ditellurides.

Organic derivatives of monocoordinated tellurium

“…11 When solutions of aldehydes contain strong acids (CF 3 COOH, PhSO 3 H, H 2 SO 4 ), dialkyl ditellurides 1 are formed as the main reaction products (yields 34% ± 56%); in this case, only traces of primary aliphatic alcohols are formed. 12 Ketones react in a similar way, but the yields of the corresponding dialkyl and di(cycloalkyl) ditellurides are lower. 12 According to the scheme proposed by the researchers cited, 12 the ditellurides 1 result from the reduction of telluroaldehydes 2 with hydrogen telluride.…”

“…12 Ketones react in a similar way, but the yields of the corresponding dialkyl and di(cycloalkyl) ditellurides are lower. 12 According to the scheme proposed by the researchers cited, 12 the ditellurides 1 result from the reduction of telluroaldehydes 2 with hydrogen telluride. The influence of pH on the outcome of these reactions is due to the fact that in strongly acidic media the acid ± base equilibrium 3 4 is almost entirely shifted to the right: a.…”

“…However, in reality, the reactions of H 2 Te, generated in situ from aluminium telluride and water, with aldehydes and ketones afford alcohols 11 or mixtures of dialkyl ditellurides with alcohols. 12 Alcohols are formed in 50% ± 100% yields when H 2 Te is passed through solutions of carbonyl compounds in THF. 11 When solutions of aldehydes contain strong acids (CF 3 COOH, PhSO 3 H, H 2 SO 4 ), dialkyl ditellurides 1 are formed as the main reaction products (yields 34% ± 56%); in this case, only traces of primary aliphatic alcohols are formed.…”