132608-32-3Relevant academic research and scientific papers
Furan-2(3H)- and -2(5H)-ones. Part 6. Di-?-methane rearrangement of the α-substituted 4-benzylfuran-2(5H)-one system
Muraoka, Osamu,Tanabe, Genzoh,Higachiura, Mie,Minematsu, Toshie,Momose, Takefumi
, p. 1437 - 1444 (1995)
The effect of the 'central methane' substitution on the di-?-methane rearrangement in 4-benzyl-2,5-dihydrofuran-2-ones 8a-d was investigated.Significant enhancement of efficiency in the rearrangement leading in high combined yields to two isomeric products, endo-12 and exo-12, is discussed in terms of both the substituent effects at the benzylic carbon and the restrained features of the ring-enrolled ?-system.The origin of the difference in chemoselectivity compared with that of the 3-benzyl counterpart 5 where a photoarylated product 6 resulted upon photoirradiation was also investigated, and was rationalized by postulating a higher reactivity at the β-position of the enone system.
ACCENTUATION OF THE DI-?-METHANE REACTIVITY BY CENTRAL CARBON SUBSTITUTION IN THE 4-(PHENYLMETHYL)-2(5H)-FURANONE SYSTEM
Muraoka, Osamu,Tanabe, Genzoh,Momose, Takefumi
, p. 1589 - 1592 (2007/10/02)
The effect of 'central methane' substitution on the di-?-methane rearrangement in 4-(phenylmethyl)-2(5H)-furanones (1b-d) was investigated.Significant enhancement of efficiency in the reaction leading in high combined yields to two isomeric products (endo-2 and exo-2) was discussed in terms of both the substituent effects at the allylic methane carbon and the restrained feature of the ring-enrolled ?-system.
