Synthesis of Terminal Ethynyl Aryl Selenides and Sulfides Based on the Retro‐Favorskii Reaction of Hydroxypropargyl Precursors

Abstract

The retro-Favorskii reaction is an excellent way to achieve terminal alkynes. Methodologies that connect the synthesis of terminal alkynes and organochalcogen motifs are important for the construction of novel compounds. Fourteen new terminal alkynes containing either C -S or C -Se bonds were selectively prepared through the retro-Favorskii reaction from the respective carbinol precursors. It was discovered that terminal chalcogen alkynes were stable for weeks if stored as a solution in hexanes.

Highly Selective Synthesis of α-Hydroxy, α-Oxy, and α-Oxo Amides by a Post-Passerini Condensation Transformation

“…9, 149.0, 145.9, 138.7, 135.8, 133.8, 131.1, 127.6, 127.4, 126.4, 71.4, 48.1, 32.7, 25.6, 25.1, 17.8 9, 149.0, 145.4, 137.7, 137.6, 133.9, 133.4, 127.7, 127.3, 127.1, 71.4, 48.1, 32.7, 25.6, 25.1, 21.6 9, 158.3, 147.3, 142.7, 137.2, 134.1, 129.4, 128.6, 123.5, 106.5, 71.4, 56.2, 48.1, 32.7, 25.6, 25. Butyl-2-(4-chlorophenyl) N-tert-Butyl-2-(2-chlorophenyl) N-tert-Butyl-2-(2-chloro-6-methoxyquinolin-3-yl) 2, 158.3, 147.3, 142.7, 137.2, 134.2, 129.4, 128.6, 123.5, 106.4, 71.5, 56.2, 50.8, 28.9. Anal. Calcd for C 16 H 19 ClN 2 O 3 (322.79): C,59.54;H,5.93;N,8.68. Found: C,59.32;H,5.84;N,8.81.…”

“…0, 158.6, 154.3, 151.4, 149.5, 131.0, 130.4, 129.6, 129.3, 128.4, 128.1, 127.23, 121.0, 114.8, 96.0, 80.8, 62.3, 39.1, 31.5, 20.0, 13.7. Anal. Calcd for C 24 H 24 N 2 O 3 (388.46): C,74.21;H,6.23;N,7.21. Found: C,74.27;H,6.19;N,7.17.…”

“…Butyl-7-methyl-3-(2-phenoxyethylidene)-1,3-dihydrofuro-[3,4-b 1, 156.5, 154.2, 151.5, 149.5, 131.0, 130.4, 130.2, 130.0, 129.4, 129.3, 128.4, 128.1, 127.2, 114.7, 96.2, 80.7, 62.5, 39.1, 31.5, 20.5, 20.0, 13.7. Anal. Calcd for C 25 H 26 N 2 O 3 (402.49): C,74.60;H,6.51;N,6.96. Found: C,74.47;H,6.57;N,6.84.…”

“…Butyl-3-[2-(p-tolyloxy)ethylidene]-1,3-dihydrofuro[3,4-b] 2, 158.6, 154.5, 150.5, 148.1, 137.4, 132.8, 130.2, 129.6, 129.3, 128.2, 127.3, 120.9, 114.9, 95.4, 80.8, 62.3, 39.1, 31.5, 20.0, 13.7. Anal. Calcd for C 25 H 26 N 2 O 3 (402.49): C,74.60,H,6.51;N,6.96. Found: C,74.67,H,6.44;N,6.82. M. Shiri et al N-Isopropyl-7-methyl-3-(2-phenoxyethylidene)-1,3-dihydrofuro[3,4-b] = 167.3, 158.7, 154.6, 150.6, 148.2, 137.3, 132.7, 130.2, 129.5, 129.3, 129.1, 128.3, 127.3, 120.9, 114.9, 95.5, 80.7, 62.3, 41.5, 22.5, 21.6. Anal.…”

“…Found: C,74.67,H,6.44;N,6.82. M. Shiri et al N-Isopropyl-7-methyl-3-(2-phenoxyethylidene)-1,3-dihydrofuro[3,4-b] = 167.3, 158.7, 154.6, 150.6, 148.2, 137.3, 132.7, 130.2, 129.5, 129.3, 129.1, 128.3, 127.3, 120.9, 114.9, 95.5, 80.7, 62.3, 41.5, 22.5, 21.6. Anal. Calcd for C 24 H 24 N 2 O 3 (388.46): C,74.21;H,6.23;N,7.21. Found: C,74.09;H,6.17;N,7.25.…”