19486-71-6Relevant articles and documents
Electrocatalytic Activation of Donor–Acceptor Cyclopropanes and Cyclobutanes: An Alternative C(sp3)?C(sp3) Cleavage Mode
Brandt, Felix,Jacob, Christoph R.,Jones, Peter G.,Kolb, Simon,Petzold, Martin,Werz, Daniel B.
, p. 15928 - 15934 (2021)
We describe the first electrochemical activation of D–A cyclopropanes and D–A cyclobutanes leading after C(sp3)?C(sp3) cleavage to the formation of highly reactive radical cations. This concept is utilized to formally insert molecula
Br?nsted Base-Catalyzed Tandem [2+4] Annulation/Tautomerization/Aromatization Reaction of α-Alkylidene Succinimides with 5-Alkenyl Thiazolones
Ge, Yanqing,Gong, Qi,Gu, Jing,Guo, Hongchao,Luo, Shan,Xie, Lei,Yang, Huimin,Yuan, Chunhao
, p. 3336 - 3347 (2021)
A Br?nsted base-catalyzed tandem [2+4] annulation/tautomerization/aromatization reaction of α-alkylidene succinimides with 5-alkenyl thiazolones has been developed for synthesis of functionalized thiazolo pyrones under mild conditions. The prepared thiazo
Selective oxidation of alcohol-d1to aldehyde-d1using MnO2
Kitsuwa, Kohei,Kumadaki, Katsushi,Nakayama, Atsushi,Okamura, Hironori,Ozawa, Keita,Shinada, Tetsuro,Tamura, Yusaku,Yamamoto, Yuki,Yasuno, Yoko
, p. 28530 - 28534 (2021/09/22)
The selective oxidation of alcohol-d1to prepare aldehyde-d1was newly developed by means of NaBD4reduction/activated MnO2oxidation. Various aldehyde-d1derivatives including aromatic and unsaturated ald
Systematic Evaluation of 1,2-Migratory Aptitude in Alkylidene Carbenes
Dale, Harvey J. A.,Nottingham, Chris,Poree, Carl,Lloyd-Jones, Guy C.
supporting information, p. 2097 - 2107 (2021/02/01)
Alkylidene carbenes undergo rapid inter- and intramolecular reactions and rearrangements, including 1,2-migrations of β-substituents to generate alkynes. Their propensity for substituent migration exerts profound influence over the broader utility of alkylidene carbene intermediates, yet prior efforts to categorize 1,2-migratory aptitude in these elusive species have been hampered by disparate modes of carbene generation, ultrashort carbene lifetimes, mechanistic ambiguities, and the need to individually prepare a series of 13C-labeled precursors. Herein we report on the rearrangement of 13C-alkylidene carbenes generated in situ by the homologation of carbonyl compounds with [13C]-Li-TMS-diazomethane, an approach that obviates the need for isotopically labeled substrates and has expedited a systematic investigation (13C{1H} NMR, DLPNO-CCSD(T)) of migratory aptitudes in an unprecedented range of more than 30 alkylidene carbenes. Hammett analyses of the reactions of 26 differentially substituted benzophenones reveal several counterintuitive features of 1,2-migration in alkylidene carbenes that may prove of utility in the study and synthetic application of unsaturated carbenes more generally.
