Allyl and benzyl iodides by the anomalous action of iodotrimethylsilane.
Iodotrimethylsilane (TMSI), routinely used for the dealkylation of ethers and esters, has been found to efficiently convert allyl and benzyl phosphotriesters into the corresponding iodides under mild, Brønsted-neutral conditions. In contrast, alkyl and aryl phosphotriesters were dealkylated to the corresponding phosphates under identical conditions.
Zhu
Qing
Q
Institute of Bioengineering, Zhejiang University of Technology, Hangzhou, Zhejiang Province 310014, PR China. chmzhuq@hotmail.com
Tremblay
Matthew S
MS
D001593:Benzyl Compounds / Q000737:chemistry; D007454:Iodides / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D001593:Benzyl Compounds; D007454:Iodides; D012821:Silanes; D014297:Trimethylsilyl Compounds; C027752:iodotrimethylsilane