Author:
Mitchell Reginald H.,Yan Joseph Shue-Hen
Abstract
The synthesis of trans-12b,12c-dimethyl-12b,12c-dihydrobenzo(e)pyrene 4, in 10 steps from o-dibromobenzene and 2,6-dichlorotoluene utilizing a Wittig rearrangement – Hofmann elimination sequence on the benzothiacyclophane 6 is described. The diatropicity of 4 is compared to the parent trans-10b,10c-dimethyl-10b,10c-dihydropyrene 1, and to other benzannelated annulenes.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
23 articles.
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1. A practical synthesis and X-ray crystal structure of tribenzo[a,d,j]corannulene;Canadian Journal of Chemistry;2017-04
2. Suppressing the Thermal Metacyclophanediene to Dihydropyrene Isomerization: Synthesis and Rearrangement of 8,16-Dicyano[2.2]metacyclophane-1,9-diene and Evidence Supporting the Proposed Biradicaloid Mechanism;The Journal of Organic Chemistry;2007-12-22
3. Synthesis and Photochromic Properties of Molecules Containing [e]-Annelated Dihydropyrenes. Two and Three Way π-Switches Based on the Dimethyldihydropyrene−Metacyclophanediene Valence Isomerization;Journal of the American Chemical Society;2003-02-19
4. Synthesis and Diatropicity of trans-N-Cyclohexyl-2‘,5‘,10b,10c-tetramethyl- pyrrolo[3,4-e]-10b,10c-dihydropyrene. The First Example of an Iso[17]annulenopyrrole;The Journal of Organic Chemistry;1997-08-01
5. Synthesis of the elusive dibenzannelated dihydropyrene dibenzo[e,l]dimethyldihydropyrene, a molecular photo-switch;Tetrahedron Letters;1996-07