A Convenient Preparation of 2,4,6-Trisubstituted 1,3,5-Triselenanes by Treating Aldehydes or Their Acetals with 2,2,4,4,6,6-Hexamethyl-1,3,5-triselena-2,4,6-tristannacyclohexane in the Presence of BF3·OEt2 and AlCl3

Abstract

A convenient preparation of 2,4,6-trisubstituted 1,3,5-triselenanes was achieved by the treatment of aldehydes or their acetals with 2,2,4,4,6,6-hexamethyl-1,3,5-triselena-2,4,6-tristannacyclohexane, (Me2SnSe)3, in the presence of BF3·OEt2 and AlCl3.

SnCl4‐Induced Unsymmetrical Cleavage of Bis(N,N‐diethylcarbamoyltelluro)‐arylmethanes: Generation of Tellurobenzaldehydes

“…We already reported that the reaction of bis( N,N ‐diethylcarbamoylseleno)methanes with SnCl 4 in the absence of trapping agents afforded β‐1,3,5‐triselenananes, the trimeric products of selenoaldehydes, in moderate‐to‐high yields . However, in spite of the exhaustive efforts, reaction of 5a – 5d with SnCl 4 only afforded a complex mixture containing the corresponding benzaldehydes and a trace amount of stilbene derivatives 7 along with the extrusion of elemental tellurium, and 1,3,5‐tritelluranes were not obtained at all in contrast with the cases of the reaction starting from the selenium analogues.…”

“…However, in spite of the exhaustive efforts, reaction of 5a – 5d with SnCl 4 only afforded a complex mixture containing the corresponding benzaldehydes and a trace amount of stilbene derivatives 7 along with the extrusion of elemental tellurium, and 1,3,5‐tritelluranes were not obtained at all in contrast with the cases of the reaction starting from the selenium analogues. However, when 5a (R 2 = C 6 H 5 ) was treated with SnCl 4 (1.5 mol) in CDCl 3 in an NMR tube and the reaction was monitored by using 1 H NMR at 298 K, a characteristic singlet signal at δ = 5.23 , assignable to the methine proton of symmetrical β‐1,3,5‐tritellurane 8a , was observed in the NMR spectrum of the reaction mixture. Furthermore, along with standing of the reaction mixture, a new singlet signal at δ = 9.70, assigned to the formyl proton of benzaldehyde, was gradually increasing along with the extrusion of elemental tellurium.…”

Synthesis of Metallacycles by Oxidative Addition of Sn−S, Sn−Se, Sn−Te, and Ge−Te Containing Precursors to Platinum(II)

“…The preliminary communication 6 reported that the reactions of [PtMe 2 (bu 2 bipy)], 1 , with [(R 2 SnS) 3 ] to give 2 or 3 occur over a period of several hours in refluxing acetone solution. The reactions of 1 with [(R 2 SnSe) 3 ] (R = Me, Ph) to give 4 and 5 , respectively, were faster, being complete within 0.5 h in refluxing acetone solution, and the products were isolated as air-stable yellow solids (Scheme ). Similar reactions of 1 with [(R 2 SnTe) 3 ] (R = Me, Ph) 7 and [(Me 2 GeTe) 3 ] yielded the new PtSn 2 Te 2 metallacycles 6 or 7 and the PtGe 2 Te 2 metallacycle 8 but were faster, being complete within seconds at room temperature in CH 2 Cl 2 solution.…”

Stannic chloride-induced unsymmetrical CSe bond cleavage of bis(N,N-dimethylcarbamoylseleno)methanes: Novel generation of selenoaldehydes

“…On the other hand, as expected, treatment of 1a-d with SnCl 4 (2.0 mol amt.) at RT under an Ar atmosphere afforded ␤-1,3,5-triselenanes 6a-d [6,10,[33][34][35], the trimers of selenoaldehydes 3a-d, as the major products along with 4 and the recovery of 1. The yields of 6a-d were efficiently improved by the use of 3.0-5.0 molar amount of SnCl 4 , and in such cases neither the stereoisomers of 6a-d nor any other bypoducts, except for trace amounts of 4 and aldehydes 7, were found in the crude products.…”