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(45) To accelerate the rate of oxidation of Sec−SeH, a base was needed.
(46) Sec−SeOH 1a exhibited a singlet corresponding to the OH proton at 5.35 ppm.
(47) 77Se NMR chemical shifts of previously reported arylmethyl- substituted selenenic acids: S12 (1243 ppm) and S13 (1261 ppm); for details, see Table S4.
(48) Cyclic selenenyl amide 14 was also obtained by the intramolecular cyclization of Sec−SeI 5 in the presence of NaOH (Scheme S26). The five-membered ring structure of 14 was determined by 2D NMR spectroscopy (Figure S12). Compound 14 was found to be less susceptible to oxidative deselenation than Sec− SeH 3b (Scheme S30, Tables S7 and S8).
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