Photo-induced molecular transformations. Part 87. Ring expansion through [2 + 2] photocycloaddition-β-scission sequences; synthesis of benzohomotropones from 1- and 2-naphthols and methyl acrylate
- 1 January 1988
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 3,p. 491-496
- https://doi.org/10.1039/p19880000491
Abstract
Photolysis of 4-substituted tricyclo[6.4.0.02,5]dodeca-1(12),6,8,10-tetraen-5-ols (9), (10), and (12), derived in three-steps from the regioselective photocycloadducts formed from 2-naphthyl trimethylsilyl ether and methyl acrylate, in the presence of HgO–I2 in benzene, to give the benzocyclo-octenone derivatives (11), (13), and (14) which arise from β-scission of their fused bond. The benzocyclo-octenones cyclized with base in DMF to give benzohomotropones, 4-substituted tricyclo[6.4.0.02,4]dodeca-1(12),6,8,10-tetraen-2-ones (15) and (16). Similar photolyses of 3-substituted tricyclo[6.4.0.02,5]dodeca-1(12),6,8,10-tetraen-2-ols (24) and (25), prepared in three steps from the regioselective [2 + 2] photocycloadduct (19) formed from 1-naphthyl trimethylsilyl ether with methyl acrylate, in the presence of HgO–I2 in benzene, gives the benzocyclo-octenone (26) in rather low yield. Treatment of the latter with a base in DMF gave a benzohomotropone, 3-substituted tricyclo[6.4.0.03,5]dodeca-1(12),6,8,10-tetraen-2-one (27).Keywords
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