Unconventional Transformation of the Two Carbonyl Groups in 4,4',5,5'-Tetrachloro-10 H,10' H-[9,9'-bianthracenylidene]-10,10'-dione into Diallenes

Org Lett. 2020 Nov 6;22(21):8629-8633. doi: 10.1021/acs.orglett.0c03233. Epub 2020 Oct 12.

Abstract

The diallene-containing compound dACl-1 was unexpectedly obtained by the unconventional transformation of two carbonyl groups in 4,4',5,5'-tetrachloro-10H,10'H-[9,9'-bianthracenylidene]-10,10'-dione into diallenes. In addition, the two 1-triisopropylsilyl (TIPS) groups in dACl-1 were easily removed to yield dACl-2. The reaction mechanism was investigated and is discussed. Moreover, both compounds are stable under ambient conditions, and, in particular, dACl-1 is thermally stable at 315 °C.