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- Title
The unexpected formation of a dihydroisobenzofuran derivative from the addition of a Grignard reagent to a 1,3-indanedione.
- Authors
Vile, James; Carta, Mariolino; Bezzu, C. Grazia; Dee, James; McKeown, Neil B.
- Abstract
Despite good literature precedents, the addition of excess 2-biphenylmagnesium bromide to 4,5-dimethoxy-1,3-indanedione, followed by acid work-up, did not give the desired diol precursor to an Organic Molecule of Intrinsic Microporosity. Instead a dihydroisobenzofuran derivative was isolated in moderate yield and its structure characterised fully by single crystal X-ray crystallography. It is suggested that this product is formed by sequential Grignard addition, retroaldol reaction, a second Grignard addition and acid-mediated formation of the dihydroisobenzofuran ring.
- Subjects
RING formation (Chemistry); X-ray crystallography; MICROPOROSITY; CRYSTAL structure; ISOBENZOFURAN; ADDITION reactions; BROMIDES; GRIGNARD reagents; CHEMICAL derivatives
- Publication
ARKIVOC: Online Journal of Organic Chemistry, 2012, p190
- ISSN
1551-7004
- Publication type
Article