69262-53-9Relevant academic research and scientific papers
Photo-allylation and photo-benzylation of carbonyl compounds using organotrifluoroborate reagents
Nishigaichi, Yutaka,Orimi, Takayuki,Takuwa, Akio
experimental part, p. 3837 - 3839 (2010/03/04)
Allyl- and benzyl-trifluoroborates can be applied to the photoreaction of carbonyl compounds to afford the corresponding alcoholic adducts in acceptable yields via a photo-induced single electron transfer pathway. The results were confirmed from the react
Regioreversed Allylation in Lewis Acid-mediated and Photochemical Addition Reactions of Unsymmetric α-Diketones with Allylic Stannanes
Takuwa, Akio,Nishigaichi, Yutaka,Yamashita, Koichi,Iwamoto, Hidetoshi
, p. 1761 - 1764 (2007/10/02)
In the photochemical reaction of allyl- and benzyltrimethylstannanes with unsymmetric α-diketones (PhCOCOR), the allylic group was introduced to the benzoyl carbon in high or excellent selectivity, whereas the acyl carbon was allylated either exclusively
Base Catalysed Rearrangements involving Ylide Intermediates. Part 18. Competing , , and Rearrangements of Ammonium Ylides
Chantrapromma, Kan,Ollis, W. David,Sutherland, Ian O.
, p. 1049 - 1062 (2007/10/02)
The rearrangements of acyl stabilised ammonium ylides are, in several cases, accompanied by competing rearrangements and in one case by a rearrangement.For examples involving migrating benzyl or phenylethyl groups the mechanism of these rearrangements has been studied.Thus the competing , , and rearrangements of the ylide (12) are largely intramolecular, but the intermolecularity is as high as 28percent for the and rearrangements and 14percent for the rearrangement in methanol at 55 deg C.The competing and rearrangements of the optically active (29a) give products with predominant retention of the configuration of the migrating phenylethyl group, but the intramolecular stereoselectivity of the rearrangement is significantly greater than that of the rearrangement.These results are consistent with a radical pair pathway for all three modes of rearrangement.Suitably substituted acyl stabilised allylammonium ylides (55) rearrange by competing , and processes.
