Journal of the Chemical Society. Perkin transactions I p. 1437 - 1444 (1995)
Update date:2022-07-29
Topics:
Muraoka, Osamu
Tanabe, Genzoh
Higachiura, Mie
Minematsu, Toshie
Momose, Takefumi
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.
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