Journal
ORGANIC LETTERS
Volume 11, Issue 22, Pages 5095-5097Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902177b
Keywords
-
Categories
Funding
- National Science Foundation [CHE-0719335]
- Maine Research Internships for Teachers and Students (MERITS) program administered by the Maine Space Grant Consortium
Ask authors/readers for more resources
The low-temperature treatment of 1,1-dibromo-1a,9b-cyclopropa[l]phenanthrene (1) with butyllithium and copper(II) chloride in THF affords a dibenzoannellated 1,2,4,6-cycloheptatetraene which undergoes a rare cyclotetramerization. The crystal structure of this formal 2 + 2 + 2 + 2 cyclotetramer (2) reveals a central eight-membered ring folded in a zigzag fashion with hydrogen atoms and exocyclic double bonds occupying axial positions. B3LYP/6-31+G** calculations indicate that the strained cyclic allene is significantly distorted and could be formed by ring expansion of a putative cyclopropylidene intermediate.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available