ISSN:
1434-1948
Keywords:
Rhodium catalysis
;
C-C coupling
;
C-H activation
;
Alkynes
;
Trisubstituted naphthalenes
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
RhCl(PPh3)3 in the presence of excess hydrochloric acid and azobenzene in refluxing 1-pentanol catalyzes the cyclodimerization of arylalkynes to 1,2,3-substituted naphthalene derivatives. This enables an easy access to 1,2,3-triphenylnaphthalene (1), 7-methoxy-1,2,3-tris(p-methoxyphenyl)naphthalene (2), 7-methyl-1,2,3-tris(p-methylphenyl)naphthalene (3), and 7-nitro-3-(p-nitrophenyl)-1,2-diphenylnaphthalene (4). A co-cyclodimerization of tolan with 4-octyne affords 3-phenyl-1,2-dipropylnaphthalene (5). The structure of 4 was resolved by single-crystal X-ray structural analysis. The rate of formation of 1 is first-order with respect to tolan and RhCl(PPh3)3 and exhibits activation parameters of ΔH
Additional Material:
7 Ill.
Type of Medium:
Electronic Resource
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