Journal of Organic Chemistry p. 4961 - 4965 (1980)
Update date:2022-08-04
Topics:
Irie, Tadashi
Tanida, Hiroshi
(2-Hydroxyethyl)- (1), (3-hydroxy-n-propyl)- (2), and (4-hydroxy-n-butyl)methyl(p-nitrophenyl)sulfonium perchlorates (3) were prepared.Products by Smiles rearrangements (intramolecular SNAr reactions) were obtained from 1 as β-(methylthio)ethyl p-nitrophenyl ether (9) in 37-42percent yield and from 2 as γ-(methylthio)propyl p-nitrophenyl ether (8) in quantitative yields, and none were obtained from 3.The rearrangement rates and yields were compared with an intermolecular SN2 reaction of dimethyl(p-nitrophenyl)sulfonium perchlorate (4) (displacement of the sulfonium group by a n-propoxy group) to estimate participation by the ω-hydroxyl oxygen.The rate ratios between the rearrangements (first order) and the SN2 n-propoxy attack (second order), effective molarities, were obtained as 6.02 * 103 M for 1 vs. 4 and 4.64 * 103 M for 2 vs. 4.
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