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This New Chemical is Fascinating But How Does it React? “Diazo-Ylide Hybrid”

🤯 This a REALLY strange but surprisingly stable and versatile chemical. We all know carbenes, but have you ever heard of carbones? This reagent reactivities you might already know from the Wittig reaction, Seyferth-Gilbert homologation and diazo chemistry. In this video, we explore its synthesis, properties with intriguing resonance structures and reactions.   / totalsynthesis   🚀 Thanks to all channel supporters!!!   / totalsynthesis_official   👉 Follow me on IG to practice more organic chemistry! https://www.total-synthesis.com 00:00 Ph3PCN2: This can really exist?! 00:26 Wittig reaction and Seyferth-Gilbert homologation 02:25 Ohira-Bestmann modification 02:52 Our crazy reagent, diphosphoranes and carbones 04:09 Interesting observations during the synthesis 06:34 X-ray, orbitals and resonance structures 08:10 Thermal stability 08:48 Reactions I: N2 as labile group 10:00 Reactions II: PPh3 as labile group 11:22 Reactions III: Carbon(0) transfer 12:57 Surprising reactions with cyclic ketones: Dimerization vs migration 14:27 THANKS for watching! Key references: - Science 2024, 385, 305 | Ph3PCN2: A stable reagent for carbon-atom transfer - JACS 1961, 83, 3539 | HEXAPHENYLCARBODIPHOSPHORANE, (C6H5)3PCP(C6H5)3 - JOC 1982, 47, 1837 | Diazoethenes: their attempted synthesis from aldehydes and aromatic ketones by way of the Horner-Emmons modification of the Wittig reaction. A facile synthesis of alkynes - Synlett 1996, 521 | An Improved One-Pot Procedure for the Synthesis Of Alkynes from Aldehydes - Interesting report on 1,2-migratory aptitudes in alkylidenes: JACS 2021, 143, 2097 | Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes Some recommended books on organic synthesis: - Clayden, Greeves, Warren; Organic Chemistry (basic organic chemistry knowledge) - Wyatt, Warren; Organic Synthesis: The Disconnection Approach (excellent introduction to retrosynthesis) - Kurti, Czako; Strategic Applications of Named Reactions in Organic Synthesis (extensive toolkit of functional group reactions and applications thereof with common conditions) - Nicolaou; Classics in Total Synthesis 1-3 (the ultimate total synthesis trilogy) - Nicolaou; Molecules That Changed the World (the world's most important molecules and their impact on everyday life) - Carreira, Kvaerno; Classics in Stereoselective Synthesis (breakdown of the fundamental and advanced methods of stereoselective synthesis and application to synthesis of stereochemically complex structures