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

✍ Scribed by Yaling Gong; Kazuaki Shimada; Hidenori Nakamura; Masamichi Fujiyama; Akihiro Kodama; Miyuki Otsuki; Rei Matsumoto; Shigenobu Aoyagi; Yuji Takikawa

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 532 KB
• Volume: 17
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20190

✦ Synopsis

Treatment of bis (N,N-dimethylcarbamoylseleno)methanes with SnCl 4 afforded β-1,3,5triselenanes in moderate to high yields, and the key intermediates of the reactions, i.e., acylselonium ions and selenoaldehydes, were successfully trapped by using allyltrimethylsilane or 2,3-dimethyl-1,3butadiene to obtain the allylation products or the cycloadducts, respectively.