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3a,8b-Dihydro-7-methoxy-8b-(trifluoromethyl)-2H-indeno[1,2-b]furan-2,4(3H)-dione

✍ Scribed by Ukerun, Sylvester Ohwevwo

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
166 KB
Volume
1989
Category
Article
ISSN
0947-3440

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✦ Synopsis

Indeno[ 1,

furan-2,4(3H)-dione derivative pentachloride gave an indanone 5, instead of the expected dihydrofuran 6. The mechanism for the formation of the indanone 5 implies the intermediate acid chloride 7. The formation of 5 instead of 6 is due to facilitation of electrophilic attack of the chlorocar-bony1 group on the aromatic nucleus by the electron-donating effect of the methoxy group. This effect is not in operation in the nonmethoxy analogue, in which prototropic rearrangement followed by elimination of HCI leads to a nonmethoxy dihydrofuran like 6.

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