1992
DOI: 10.1246/cl.1992.1389
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A Convenient Synthesis of Unsymmetrical Tellurides by a Sequential Reductive Cleavage of Bis(N,N-dimethylcarbamoyl) Ditelluride

Abstract: Bis(N,N-dimethylcarbamoyl) ditelluride was converted to unsymmetrical tellurides possessing various substituents by a convenient stepwise reduction-alkylation or reduction-addition sequence.

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Cited by 20 publications
(5 citation statements)
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“…Bis( N,N ‐dimethylcarbamoyl) ditelluride ( 1 ) was at first prepared in moderate yield by treating N,N ‐dimethylformamide (DMF) with sodium and elemental tellurium under heating followed by aerobic oxidation of the reaction mixture . Preparation of bis( N,N ‐diethylcarbamoyl) ditelluride ( 2 , R 1 = C 2 H 5 ) was also carried out by treating N,N ‐diethylformamide (DEF) with lithium metal and elemental tellurium through a similar procedure as shown in Scheme .…”
Section: Resultsmentioning
confidence: 99%
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“…Bis( N,N ‐dimethylcarbamoyl) ditelluride ( 1 ) was at first prepared in moderate yield by treating N,N ‐dimethylformamide (DMF) with sodium and elemental tellurium under heating followed by aerobic oxidation of the reaction mixture . Preparation of bis( N,N ‐diethylcarbamoyl) ditelluride ( 2 , R 1 = C 2 H 5 ) was also carried out by treating N,N ‐diethylformamide (DEF) with lithium metal and elemental tellurium through a similar procedure as shown in Scheme .…”
Section: Resultsmentioning
confidence: 99%
“…However, only limited research works on generation, trapping, or metal complexation of telluroaldehydes B were reported due to the high instability of the target species toward air, light, and heating, as well as the lack of preparative methods of suitable and easily accessible precursors. In the course of our studies on the novel generation of higher‐row chalcogenocarbonyl compounds, we previously reported a convenient preparation of stable ditelluroacetal derivatives A through the reaction of in situ generated tellurocarbamate ions with gem‐dihaloalkanes . Actually, such ditelluroacetals A are recognized as potent precursors for telluroaldehydes B in the light of their symmetrical structures with an easily removable electron‐withdrawing carbamoyl group on each tellurium atom, and compouds A are expected to undergo SnCl 4 ‐induced unsymmetrical C–Te bond cleavage to generate telluroaldehydes B through push–pull type removal of N,N ‐diethyltellurocarbamate in an analogous manner of our previous report on the generation of selenoaldehydes from bis( N,N ‐dimethylcarbamoylseleno)methanes .…”
Section: Introductionmentioning
confidence: 99%
“…Subsequently, stepwise treatment of a DMF solution of diselenide 4 with NaH [31,32] and a gem-dihaloalkane 5 (benzal bromide 5a, m-chlorobenzal bromide 5b, pchlorobenzal bromide 5c, 1,1-dibromoethane 5d, dibromomethane 5e, and ethyl dichloroacetate 5f, respectively) efficiently afforded air-stable bis(N,Ndimethylcarbamoylseleno)methanes 1a-f [26], which are regarded as a new class of symmetrical diselenoacetals bearing a N,N-dimethylcarbamoyl group on each selenium atoms. On the other hand, stepwise treatment of 4 with NaBH 4 with 5a in a mixed solvent of C 2 H 5 OH-DMF (1:1) only gave 1a in 20% yield along with the formation of dibenzyl diselenide as a major product [31], and the use of diisobutylaluminum hydride (DIBAH), in place of NaH, also gave discourageous results.…”
Section: Stepwise Preparation Of Bis(nn-dimethylcarbamoylseleno)methmentioning
confidence: 99%
“…However, to date, conversion of symmetrical diseleno-or ditelluroacetals into the corresponding chalcogenoaldehydes or chalcogenoketones was not studied at all due to the lack of preparative method of such precursors bearing a suitable chalcogenprotecting group on each chalcogen atoms in spite of their potent synthetic convenience. In the course of our studies on the novel generation of highly reactive species related to higher row chalcogenocarbonyl compounds, we previously reported a convenient preparation of stable ditelluroacetal derivatives 2 using the reaction of N,N-dimethyltellurocarbamate ions with gem-dihaloalkanes [17,26]. These results urged us to the preparation of symmetrical diselenoacetals 1 and the further reactions of 1 with a Lewis acid on the basis of the coordinating interaction between the selenocarbamate moiety and a soft Lewis acid [27].…”
Section: Introductionmentioning
confidence: 99%
“…In order to make this transformation practically useful for organic synthesis, general and convenient synthetic methods of carbamotelluroates are strongly demanded. The hitherto known methods for their preparation are limited only to the substitution of carbamoyl chlorides with tellurolates [ 1 b] and telluration of N,N-dimethylformamide [2]. As for the selenium analogues, Se-alkyl carbamoselenoates were obtained in good yields by the alkylation with alkyl halides of ammonium carbamoselenoates generated in situ from selenium, carbon monoxide, and secondary amines [3].…”
mentioning
confidence: 99%