Anaerobic photocyclization of ortho-dialkylamino substituted stiff-stilbenes
Journal
Journal of the Chinese Chemical Society
Date Issued
2024-01-01
Author(s)
Abstract
The photocyclization of diarylethenes toward polycyclic aromatic hydrocarbons and analogs has been well-documented. However, stiff-stilbene was reported to be inactive, and examples of photocyclization-induced deamination remain unknown. Here, we report that ortho-(N,N-dimethylamino)-stiff-stilbene (1a) undergoes efficient photocyclization-induced deamination, forming the dicyclopenta-fused phenanthrene (DCPP) with good yield (65%) under anaerobic conditions. The relative reactivities of stiff-stilbenes with different o-amino substituents (1b–1g) or with an o-methoxy (1h) group, and those of o-(N,N-dimethylamino)stilbenes (2a and 2aMe), provide insights into the substituent and structural effects.
Subjects
organic chemistry | organic Synthesis | photochemistry
Type
journal article