54537-52-9Relevant academic research and scientific papers
4,7-Diphenylisobenzofuran: A useful intermediate for the construction of phenyl-substituted acenes
Rainbolt, James Eric,Miller, Glen P.
, p. 3020 - 3030 (2007/10/03)
(Chemical Equation Presented) The formation and subsequent reactivity of previously unknown 4,7-diphenylisobenzofuran, 5, is reported. The Diels-Alder reaction between 5 and p-benzoquinone in boiling glacial acetic acid yields an unprecedented exo,exo ant
Furan-2(3H)- and -2(5H)-ones. Part 8. Conformation and di-π-methane reactivity of the 4,7-disubstituted tetrahydroisobenzofuran-1-one system: A mechanistic and exploratory study
Muraoka, Osamu,Tanabe, Genzoh,Yamamoto, Emi,Ono, Masaru,Minematsu, Toshie,Kimura, Takayoshi
, p. 2879 - 2890 (2007/10/03)
Photoirradiation of cis- and trans-4-7-diphenyl-1,3,4,7-tetrahydroisobenzofuran-1-one cis- and trans-14 and its 4-methyl analogues cis- and trans-15 afford the corresponding di-π-methane rearrangement products 27, 28 and 24 in moderate yields. MM2 calculations for the cis- and trans-4,7-diphenyl substrates cis- and trans-14 showed that the planar structure is most stable for both compounds and that the molecular energy difference between the planar structure and the boat conformation is small enough for a boat-planar-boat conversion. On the basis of the calculations, the di-π-methane rearrangement of the compounds 14 and 15 is supposed to proceed via the boat conformation with a pseudoaxial phenyl substituent. An X-ray structure determination of the two diphenyl substrates cis- and trans-14 provides strong support for the validity of the calculations in predicting optimum structures for cis- and trans-disubstituted tetrahydroisobenzofuranone.
Ring-chain tautomerism as a factor in the reaction between Grignard reagents and substituted phthalides
Smith,Wikman
, p. 2603 - 2611 (2007/10/04)
With phthalide two equivalents of Grignard reagent react rapidly in a reaction which could not be controlled to give stepwise addition. In contrast, 3,3- and 4,7-disubstituted phthalides react with only one equivalent of organometallic reagent. The primary addition product formed from one equivalent each of phthalide and Grignard reagent exists in a ring-chain tautomerism whose position is controlled by the interaction between the substituents present in the phthalide and the alkyl group introduced by the Grignard reagent. With substituted phthalides, ring opening of the primary addition product is prevented by these interactions and thus a second equivalent of Grignard reagent does not react. In the absence of substituents, ring opening and the reaction of a second equivalent occurs. Somewhat related effects appear to exist in the reaction between Grignard reagents and phthalic anhydride and in the dehydration of substituted phthalyl alcohols to their corresponding phthalans.
