155586-44-0Relevant articles and documents
New Intramolecular Five-Endo-Mode Cyclization of Allenyl Aryl Ketones
Nagao, Yoshimitsu,Lee, Woo-Song,Kim, Kweon
, p. 389 - 392 (1994)
A convenient preparation of allenyl aryl ketones was achieved by the Weinreb-modified Grignard reaction of N-methoxy-N-methylamides with propargylmagnesium bromide.On treatment with BF3*OEt2, the allenyl aryl ketones were converted to methylenebenzocyclopentenones via a new 5-endo-mode cyclization.
InI3- or ZnI2-catalyzed reaction of hydroxylated 1,5-allenynes with thiols: A new access to 3,5-disubstituted toluene derivatives
Ma, Jie,Peng, Lingling,Zhang, Xiu,Zhang, Zhe,Campbell, Melody,Wang, Jianbo
, p. 2214 - 2220 (2011/06/19)
Transition-metal-activated alkynes or allenes can accept nucleophilic attack and undergo direct addition of the nucleophiles to the unsaturated bonds or trigger subsequent rearrangement reactions. This chemistry has witnessed increasing development in recent years. In this report, we have focused on the metal-catalyzed reactions of a variety of substituted propargyl allenic alcohols and thiophenols using indiumACHTUNGTRENUNG(III) and zinc(II) catalysts, which can activate both the alcohol and alkyne. In this reaction, thio groups play the role of a nucleophile and trigger subsequent rearrangements to give benzene derivatives. The products can be further transformed into various 1,3,5-trisubstituted aromatic compounds by nickel-catalyzed coupling reactions through the cleavage of the C-S bonds.
Isomerizations on silica gel: Synthesis of allenyl ketones and the first Nazarov cyclizations of vinyl allenyl ketones
Stephen,Hashmi,Bats, Jan W.,Choi, Ji-Hyun,Schwarz, Lothar
, p. 7491 - 7494 (2007/10/03)
Dess-Martin oxidation followed by the chromatographic workup of crude, terminal propargyl ketones 5 on silica gel directly leads to terminal allenyl ketones 6. When the other substituent on 5 was electron-rich, 7 was observed as side-product. If the other substituent on 5 was electron-poor, the isomeric 1-propynyl ketone 8 was the side-product. Chromatography of the crude propargyl vinyl ketones 10 on silica gel delivers the products of a Nazarov cyclization.
