Synthesis of Functionalized Cyclobutane‐Fused Naphthalene Derivatives via Cascade Reactions of Allenynes with tert‐Butyl Nitrite.

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 FROM AUTHOR]