Beyond Wittig Olefination: Phosphorus Ylide as a Ring-Expansion Reagent for Dibenzocycloheptanone Synthesis.

Lin Li, Haozhe Zha, Xiaoping Xue, Longhui Duan, Zhenhua Gu

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Article in JACS Au, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

5 authors.

Lin LiHefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.

Haozhe ZhaHefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.

Xiaoping XueCollege of Science, Henan Agricultural University, Zhengzhou, Henan 450002, P. R. China.

Longhui DuanHefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.

Zhenhua GuHefei National Research Center for Physical Sciences at the Microscale and Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, P. R. China.ORCID https://orcid.org/0000-0001-8168-2012

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We report an unprecedented transformation between phenanthrene-9,10-diones and phosphorus ylide, where methylenetriphenylphosphane exhibits dual reactivity patterns, enabling both olefination and ring expansion to construct seven-membered carbocycles in moderate to good yields. This process proceeds through initial Wittig olefination followed by an unusual alkenyl group 1,2-migration pathway from either an oxaphosphetane or betaine intermediate. Mechanistic studies, including deuterium-labeling experiments and isolation of key intermediates, support a pathway involving conformationally controlled ring expansion.

Indexed as

dibenzocycloheptanonedibenzo-cycloheptenoneolefinationring-expansionylides

Identifiers

PMID41450635

DOI10.1021/jacsau.5c01138

PMCPMC12728619

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