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An Unexpected Synthesis of Crowded Triphenylenes
In attempts to make octaphenyldibenzofuran ( 7 ) and octaphenyldibenzothiophene ( 8 ), 2,5‐dibromofuran ( 4 ) and 2,5‐dibromothiophene ( 5 ), respectively, were heated with tetracyclone ( 2 ) under forcing conditions, but only single addition products, such as 2‐bromo‐4,5,6,7‐tetraphenylbenzofuran (...
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| Published in: | European journal of organic chemistry 2023-11, Vol.26 (42) |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites |
| Online Access: | Get full text |
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| Summary: | In attempts to make octaphenyldibenzofuran (
7
) and octaphenyldibenzothiophene (
8
), 2,5‐dibromofuran (
4
) and 2,5‐dibromothiophene (
5
), respectively, were heated with tetracyclone (
2
) under forcing conditions, but only single addition products, such as 2‐bromo‐4,5,6,7‐tetraphenylbenzofuran (
10
) and 2‐bromo‐4,5,6,7‐tetraphenylbenzothiophene (
12
) were observed. However, when 2,5‐dibromothiophene‐1,1‐dioxide (
6
) was heated with tetracyclone, the chief product was 1,2,3,4,6,7,8‐heptaphenyltriphenylene (
14
). Similarly, when compound
6
was heated with acecyclone (
15
), the product was 11,18,20‐triphenyldiacenaphtho[
a,h
]triphenylene (
16
). Both
14
and
16
have been characterized by X‐ray crystallography. They are proposed to form from double Diels‐Alder addition products of the cyclopentadienones by extrusion of sulfur dioxide and rearrangement of the resulting radicals. |
|---|---|
| ISSN: | 1434-193X 1099-0690 |
| DOI: | 10.1002/ejoc.202300708 |