4861-59-0Relevant academic research and scientific papers
sp3-Carbon detosylations by Dibal-H: model studies
Janssen, Cornelus G. M.,Hendriks, Adrianus H. M.,Godefroi, Erik F.
, p. 220 - 224 (2007/10/02)
α- And β-tosylated alkenylaromatic systems 5c,d and 9a-c are cyclized to 6c,d and 10a-c in FSO3H-containing SO2 in synthetically useful processes.Dibal-H treatment of α-substituted 6c,d brings about rapid, high-yield detosylation to 7c,d; the β-tosylated isomers 10a-c give, with Dibal-H, after 18 h in refluxing toluene, mainly unreacted sulfones together with minor amounts of sulfides 11a-c.Ring-disrupted congeners 15a-d and 18a-c behave likewise, with α-tosylated 15a-d being rapidly detosylated by Dibal-H to 16a-d and their β-substituted isomers undergoing low-yield reductions to sulfides 19a-c.Dibal-H mediated detosylation appears to be limited to benzylic substrates.
