Synthesis of Functionalized Cyclobutane‐Fused Naphthalene Derivatives via Cascade Reactions of Allenynes with tert‐Butyl Nitrite. Issue 6 (29th January 2019)

• Record Type: Journal Article
• Authors: Feng, Tian; He, Yan; Zhang, Xinying; Fan, Xuesen
• Is Part Of: Advanced synthesis & catalysis. Volume 361:Issue 6(2019)
• Page Start: 1271
• Page End: 1276
• Publication Date: 2019-01-29
• Subjects: Cyclobutanol-fused 2-nitronaphthalen-1-ols -- Nitrocyclobutane-fused naphthalene-1, 2-diones -- Benzene-linked allenynes -- tert-Butyl nitrite -- Cascade reactions; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201801439
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: A novel synthesis of cyclobutanol‐fused 2‐nitronaphthalen‐1‐ols and nitrocyclobutane‐fused naphthalene‐1, 2‐diones through cascade reactions of benzene‐linked allenynes with tert ‐butyl nitrite is presented. The formation of the title compounds involves a tandem process including allenyne [2+2] cycloaddition, radical addition onto the in situ formed cyclobutenyl moiety followed by radical coupling/oxidation. Interestingly, different kinds of functionalized naphthalene derivatives could be obtained selectively from the same substrates, and the selectivity was easily controlled by finely tuning the reaction conditions. Abstract :