ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Mesitylallene (6a), 1-mesityl-3-methyl-allene (6b) and 1-mesityl-3, 3-dimethylallene (6c) were prepared via dienol-benzene-rearrangements. At 170° 6a isomerises to give 5, 7-dimethyl-1, 2-dihydronaphthalene (8). Under the same conditions 6b rearranges to give 2, 5, 7-trimethyl-1, 2-dihydronaphthalene (10; 60%) and cis-1-mesitylbuta-1, 3-diene (11; 40%) while 6c gives only cis-1-mesityl-3-methyl-buta-1, 3-diene (13). The allenes undergo first an aromatic [1, 5 s]-sigmatropic H-shift to the o-xylylene derivatives 7, 9 and 12, which then exhibit disrotatory ring closure to the dihydronaphthalenes or aromatic [1, 7 a]-sigmatropic H-shift to the 1-mesitylbuta-1, 3-dienes.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19700530540
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