1980
DOI: 10.1021/jo01311a045
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Regioselective acid-catalyzed cyclodimerization of 1,2-dihydronaphthalene. Mechanism of formation and single-crystal x-ray analysis of two octahydrobenzo[j]fluoranthenes

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Cited by 12 publications
(4 citation statements)
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“…3,5-Dimethyl phenylboronic acid afforded the desired 3e in comparable 84% yield, while bulky 2,6-dimethyl phenylboronic acid was unsuitable in this transformation (Table , entries 4–5). Interestingly, arylboronic acids bearing methoxy substituents at 4-positions provided the corresponding product 3g in lower yield compared to other moieties bearing electron-donating groups, affording a significant amount of byproduct such as 2-amino quinoline and 4,4′-dimethoxy-1,1′-biphenyl. Functional groups, such as naphthyl and biphenyl, were also tolerated with observed yields ranging from 69 to 85% (Table , entries 7–9).…”
Section: Results and Discussionmentioning
confidence: 99%
“…3,5-Dimethyl phenylboronic acid afforded the desired 3e in comparable 84% yield, while bulky 2,6-dimethyl phenylboronic acid was unsuitable in this transformation (Table , entries 4–5). Interestingly, arylboronic acids bearing methoxy substituents at 4-positions provided the corresponding product 3g in lower yield compared to other moieties bearing electron-donating groups, affording a significant amount of byproduct such as 2-amino quinoline and 4,4′-dimethoxy-1,1′-biphenyl. Functional groups, such as naphthyl and biphenyl, were also tolerated with observed yields ranging from 69 to 85% (Table , entries 7–9).…”
Section: Results and Discussionmentioning
confidence: 99%
“…Found: C, 78.44; H, 7.72. 1,2‘-Binaphthyl (27.7 mg, 0.11 mmol, 37%) mp 74−76 °C (lit . mp 79−81 °C) was also obtained as a side product by washing the column with the same eluent.…”
Section: Methodsmentioning
confidence: 99%
“…Due to the fact that the two substrates, 5a and 5b, led to exactly the same product, the reactions proceed in all likelihood via intermediary occurring 1,2-dihydronaphthalene, subsequently dimerises under the reaction conditions to the binaphthalene 6, as already reported. [14][15][16] Thus, the elimination reaction primarily gave the desired elimination product in acceptable yields.…”
mentioning
confidence: 96%