Exploring the Skeletal Rearrangement/Self-Ring-Opening Reaction of Dibenzo[<i>b</i>,<i>f</i>][1,5]diphosphacines
This study reports the first self-ring-opening reaction of a novel eight-membered heterocyclic skeleton, dibenzo[<i>b,f</i>][1,5]diphosphacyclooctatetraene (PCOT), into (<i>Z</i>)-alkenyldiphosphines, which involves the sequential cleavage of two phosphonium-ylide bonds and the formation of a C═C bond. Theoretical analyses further rationalize the stereoselective formation of <i>Z</i>-form products and the chemical driving force behind the phosphonium-ylide (P<sup>1</sup>═C<sup>1</sup>) bond cleavage. This work represents the first example of π-conjugated eight-membered phosphacycles featuring two internal phosphonium-ylide bonds and their self-ring-opening rearrangement.
Authors
- Hongli Bao (ORCID: https://orcid.org/0000-0003-1030-5089)
- Haiyang Huang (ORCID: https://orcid.org/0000-0002-5520-0945)
- Shiyuan Lv
Institutions
- Fujian Normal University (CN)
- Chinese Academy of Sciences (CN)
- Jiangxi Science and Technology Normal University (CN)
- Fujian Institute of Research on the Structure of Matter (CN)
- Institute of Organic Chemistry (HU)
- Chemical Synthesis Lab (SG)
- University of Chinese Academy of Sciences (CN)
- State Key Laboratory of Structural Chemistry
Publication Details
- Journal
- Organic Letters
- Published
- 2025-04-15
- DOI
- https://doi.org/10.1021/acs.orglett.5c00496
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.00
Funders
- National Natural Science Foundation of China
- Haixi Institute, Chinese Academy of Sciences