Preparation of Alkynes, Part 1: By Elimination

This video is about the properties and significance of alkynes, and about the preparation of alkynes by elimination reactions. These include dehydrohalogenations and the elimination of a number of other leaving groups. You'll find here many specific examples with complete experimental details. I've also included a discussion of potential side reactions and other problems of these reactions.
Further examples (patents are available at worldwide.espa...
Org. Syn. 2016, 93, 245 (bromide, BuLi); 2010, 87, 231 (bromide, Cu); 2008, 85, 45 (fluoride, BuLi); 2007, 84, 77 (chloride, LDA); 2005, 82, 179 (bromide, KOH); 1995, 72, 252 (bromide, NaNH2); 1987, 65, 68 (chloride, NaNH2); 1979, 59, 10 (bromide, Bu4NOH); 1976, 55, 52 (hydrazone); 1958, 38, 70 (KOH); 1954, 34, 42 (bishydrazone oxidation); 1950, 30, 72 (bromide, NaNH2); 1945, 25, 92 (bromide, KOH); 1942, 22, 50 (bromide, KOH); 1938, 18, 3 (bromide, KOH); 1922, 2, 67 (bromide, KOH);
Tetrahedron Lett. 2021, 71, 153051 (bromide, K2CO3); Org. Biomol. Chem. 2020, 18, 3797-3817 (review);
Molecules 2018, 23, 2442 (review, C2H2); J. Org. Chem. 2017, 82, 5538-5556;
Chem. Pharm. Bull. 2015, 63, 393-396 (triflate, TBAF); Adv. Syn. Catal. 2015, 357, 553-560 (bromide, TBAF);
J. Org. Chem. 2014, 79, 6037-6046 (diazo); Chem. Comm. 2010, 46, 3235-3249 (bromide);
Chem. Soc. Rev. 2010, 39, 2007-2017 (review); Org. Lett. 2009, 11, 1445-1448 (acetate, DABCO);
Synlett 2008, 3091-3105 (bromide, DBU); Tetrahedron Lett. 2008, 49, 4596-4600 (fluoride);
Tetrahedron 2008, 64, 10250-10257 (bromide, Bu4NOH); Chem. Rev. 2006, 106, 5387-5412 (review);
J. Org. Chem. 2006, 71, 1902-1910 (bromide); Tetrahedron 2005, 61, 4043-4052 (bromide, DBU);
Tetrahedron Lett. 2005, 46, 6473-6476 (diazo); Acc. Chem. Res. 2005, 38, 679-686 (PhI);
Tetrahedron Lett. 2004, 45, 5597-5599 (diazo); J. Org. Chem. 2002, 67, 640-647 (sulfinate);
1999, 64, 6918-6920 (tosylate, chloride); 1997, 62, 4142-4147 (hydrazone);
Chem. Pharm. Bull. 1982, 30, 1041-1042 (hydrazone); J. Org. Chem. 1966, 31, 624-625 (hydrazone).

[@newuser871]

This kind of valuable presentations are very rare on RUclips. Thanks a lot. I want to contribute the topic with a reference for preparation of terminal alkynes; 10.1080/00397911.2017.1376334

[@florenciozaragoza]

Thanks for the reference. Yes, elimination is a good strategy. I am always amazed that almost no substitution occurs. Thank you.