The photochemistry of 2-acetoxynaphthalen-1(2H)-ones

Greenland, Harry; Pinhey, John T.; Sternhell, S.

doi:10.1039/p19860001789

Cited by 5 publications

(2 citation statements)

References 9 publications

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“…Synihesis of Naphthalen-l(2H)-ones (l), (8), and (12).-Our method for the arylation of phenols with aryl-lead triacetates l o was used to obtain the naphthalen-l(2H)-ones (1) and (8). Treatment of 2-methyl-1-naphthol with p-tolyl-lead triacetate at room temperature in chloroform containing pyridine produced compound (1) (5 l%), while reaction of 2,4-dimethyl-1 -naphthol ' with p-methoxyphenyl-lead triacetate under the same conditions gave naphthalenone (8) in good yield (68%).…”

Section: 257 -mentioning

confidence: 99%

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The photochemistry of 2,2-dimethyl- and 2-aryl-2-methylnaphthalen-1(2H)-ones. Substitution requirement for the oxadi-π-methane rearrangement

Greenland¹,

Kozyrod²,

Pinhey³

1986

J. Chem. Soc., Perkin Trans. 1

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The photochemistry of 2-aryl-2-methylnaphthalen-1 (2H) -ones (1 ) and (2), 2,2-dimethylnaphthalen-1 (2H)-one (6), 2,2,3-trimethyInaphthalen-l(2H)-one ( 7 ) , 2,2,4-trimethylnaphthalen-1 (2H)-one tetramethylnaphthalen-1 (2H)-one (1 2) has been examined. The compounds which did not contain a 4-substituent, (l), ( Z ) , (6), and ( 7 ) , were virtually unchanged under conditions which caused the 4-methyl derivative (3) to undergo an oxadi-n-methane (ODPM) rearrangement to the 1,l a-dihydrocycloprop[a]indenone (4). Similar reactivity was shown by the 4-methyl derivative (8), which gave the ODPM rearrangement products ( 9) and (10). On further irradiation, both ( 9) and (10) underwent rearrangement t o 4-(p-methoxyphenyl)-3,4-dimethylnaphthalen-l(4H)-one (11). The 4-methyl group in (3) and ( 8) would appear t o be exerting a steric effect, since irradiation of 2,2,5,7-tetramethylnaphthalen-l(2H) -one (1 2) produced the 1 -naphthol (1 3) and the 1 -tetralone (14), both of which arise from further reaction of an ODPM rearrangement product. Syntheses of the naphthalen-l(2H)-ones (l), (8), and (12) are reported.(3), 2-(p-methoxyphenyl) -2,4-dimethylnaphthalen-l(2H)-one (8), and

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Section: 257 -mentioning

confidence: 99%

“…in the same solvent system to yield exo-1-(p-methoxyphenyl)-1,l a-dimethyll,la-dihydrocycloprop[a]inden-6(6aH)-one (9) (0.43 g, 43%) as colourless needles, m.p. 1…”

Section: Irradiation Of 2-(p-methoxyphenyl)-24-dimethylnaphthal-mentioning

confidence: 99%