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Synthesis of Functionalized Cyclobutane‐Fused Naphthalene Derivatives via Cascade Reactions of Allenynes with tert ‐Butyl Nitrite
Author(s) -
Feng Tian,
He Yan,
Zhang Xinying,
Fan Xuesen
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201801439
Subject(s) - chemistry , naphthalene , moiety , nitrite , cycloaddition , selectivity , benzene , cascade , cyclobutane , cascade reaction , tandem , photochemistry , combinatorial chemistry , organic chemistry , ring (chemistry) , catalysis , materials science , chromatography , nitrate , composite material
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.