2‐(2‐Ethoxy‐2‐oxoethyl)‐1,1,3,3‐tetramethylthiouronium bromide

Tetrahydropyran synthesis mediated by catalytic triflic acid and hexafluoroisopropanol

“…The sum formulas of the detected ions were determined using Bruker Compass DataAnalysis 4.1 based on the mass accuracy (Δm/z ≤ 5 ppm) and isotopic pattern matching (SmartFormula algorithm). All 1 H NMR, 13 C DEPTQ-135 NMR, and 13 C CPD NMR spectra were recorded using a Bruker AV-400, AV-500, AV-600, or AV-700 spectrometer at 300 K. Chemical shifts are given in parts per million (ppm, δ), referenced to the solvent peak of CDCl 3 , defined at δ = 7.26 ppm ( 1 H NMR) and δ = 77.16 ppm ( 13 C NMR) [19].…”

“…Following the general procedure, 2b was isolated as a colorless oil (40 mg, 0.18 mmol, 91%). 1 H NMR (400 MHz, CDCl 3 ): δ = 7.32-7.26 (m, 2H), 7.24-7.14 (m, 3H), 3.58-3.41 (m, 1H), 2.76 (ddd, J = 14.5, 9.3, 5.5 Hz, 1H), 2.66 (ddd, J = 13.8, 9.0, 7.4 Hz, 1H), 1.89-1.76 (m, 1H), 1.71-1.59 (m, 3H), 1.58-1.50 (m, 1H), 1.49-1.33 (m, 2H), 1.24 (s, 3H), 1.18 (s, 3H), 1.17-1.08 (m, 1H) ppm; 13 O) Following the general procedure, 2c was isolated as a colorless oil (43 mg, 0.18 mmol, 89%). 1 H NMR (400 MHz, CDCl 3 ): δ = 3.59-3.33 (m, 1H), 1.69-1.59 (m, 2H), 1.59-1.51 (m, 1H), 1.43 (ddd, J = 6.8, 5.9, 2.5 Hz, 2H), 1.39-1.23 (m, 16H), 1.19 (s, 3H), 1.17 (s, 3H), 1.11-0.97 (m, 1H), 0.87 (t, J = 6.8 Hz, 3H) ppm; 13…”

“…Following the general procedure, 1b was isolated as a colorless oil (304 mg, 1.39 mmol, 70%) after purification by column chromatography (heptane/ethyl acetate = 5:1, R f = 0.29). 1 H NMR (400 MHz, CDCl 3 ): δ = 7.34-7.27 (m, 2H), 7.23-7.15 (m, 3H), 4.69 (d, J = 15.2 Hz, 2H), 3.64 (dd, J = 7.6, 4.6 Hz, 1H), 2.89-2.74 (m, 1H), 2.68 (ddd, J = 13.7, 9.5, 6.8 Hz, 1H), 2.02 (t, J = 6.3 Hz, 2H), 1.86-1.74 (m, 2H), 1.71 (s, 3H), 1.63-1.57 (m, 2H), 1.54-1.41 (m, 2H), 1.34 (t, J = 3.9 Hz, 1H) ppm; 13 2-Methylpentadec-1-en-6-ol (1c, C 16 H 32 O) Following the general procedure, 1c was isolated as a colorless solid (315 mg, 1.31 mmol, 66%) after purification by column chromatography (heptane/ethyl acetate = 5:1, R f = 0.37). 1 H NMR (400 MHz, CDCl 3 ): δ = 4.69 (d, J = 11.0 Hz, 2H), 3.60 (br s, 1H), 2.03 (t, J = 7.4 Hz, 2H), 1.72 (s, 3H), 1.68-1.36 (m, 7H), 1.35-1.20 (m, 14H), 0.88 (t, J = 6.8 Hz, 3H) ppm; 13 C NMR (101 MHz, CDCl 3 ): δ = 146.0, 110.1, 72.1, 37.9, 37.7, 37.2, 32.0, 29.9, 29.8, 29.7, 29.…”

“…Following the general procedure, 2a was isolated as a colorless oil (24 mg, 0.18 mmol, 92%). 1 H NMR (400 MHz, CDCl 3 ): δ = 3.67 (dqd, J = 12.2, 6.1, 2.2 Hz, 1H), 1.63 (ddt, J = 8.0, 7.0, 3.7 Hz, 2H), 1.54 (ddd, J = 12.8, 3.9, 2.5 Hz, 1H), 1.48-1.29 (m, 2H), 1.20 (d, J = 5.2 Hz, 6H), 1.11 (d, J = 6.1 Hz, 3H), 1.14-1.02 (m, 1H) ppm; 13…”

“…As part of our ongoing research on alkene functionalization [13] and complemented by a serendipitous discovery, we observed the hydroalkoxylation of alkenes in the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP).…”