88089-52-5Relevant articles and documents
Synthesis of α-Ketoimidoyl Fluorides via Geminal Fluorine-Promoted Azide Rearrangement
Kim, Ha Eun,Choi, Jun-Ho,Chung, Won-Jin
supporting information, p. 8810 - 8815 (2021/11/20)
Despite the promising synthetic potential, the utilization of imidoyl fluorides has been hampered by the lack of broadly applicable preparative methods. Herein, bench-stable α-ketoimidoyl fluorides were synthesized from geminal chlorofluorides through tandem azidation/rearrangement under mild conditions. The efficiency was consistently high, regardless of the steric and electronic environments. The synthetic utility of the α-ketoimidoyl fluoride was also demonstrated. Furthermore, the remarkable accelerating effect of the geminal fluorine substituent was identified and rationalized by density functional theory calculation.
A convenient method for the preparation of α-vinylfurans by phosphine-initiated reactions of various substituted enynes bearing a carbonyl group with aldehydes
Kuroda, Hirofumi,Hanaki, Emi,Izawa, Hironori,Kano, Michiko,Itahashi, Hiromi
, p. 1913 - 1920 (2007/10/03)
α-Vinylfurans were obtained by phosphine-initiated cyclization of various enynes bearing a carbonyl group at the ene end in the presence of various aldehydes, in moderate to high yields. The reaction may consist of 1,6-addition of phosphine to the enynes, ring closure, and Wittig reaction between the ylid resulting from cyclization and an aldehyde. Thus, various aldehydes were able to be used in the reaction. The reaction was influenced greatly by the substituents at the acetylene position (R1) and the α-position of the carbonyl group (R3).
Transition metal-catalyzed oxidations. 12 : α-Chlorination of silylenol ethers with tert-butyl hydroperoxide and TiCl2(OiPr)2
Krohn, Karsten,Steingroever, Klaus,Vinke, Ingeborg
, p. 62 - 64 (2007/10/03)
Enolsilyl ethers (4, 6, 8, 10, 12, 14) are chlorinated to the α-monochloro ketones (5, 7, 9, 11, 13, 15) with tert-butyl hydroperoxide in the presence of dichlorotitanium diisopropoxide in 69 - 92% yield. WILEY-VCH Verlag GmbH, 1999.