Citation: Jiang WANG, Hui Tong TANG, Pang ZHANG, Thomas C. W. MAK, Ze Ying ZHANG. Further Report on A Novel Scission of Alkyl Carbonyl C-C Bond by Substituted 4-Hydroxyacetophenones[J]. Chinese Chemical Letters, ;1998, 9(10): 899-902. shu

Further Report on A Novel Scission of Alkyl Carbonyl C-C Bond by Substituted 4-Hydroxyacetophenones

1.
Department of Chemistry, Peking University, Beijing 100871;
2.
Department of Chemistry, Chinese University of Hong Kong, Hong Kong

Received Date: 6 April 1998

Fund Project: We are grateful to the National Natural Science Foundation and the National Commission of Education for financial grants.

3-Methoxy-,3, 5-dimethoxy-, and 3-pheny 1-4-hydroxyacetophenones suffered alkyl carbonyl C-C bond scission to yield 4-hydroxybenzoate esters and 4-isopropenylphenols under standard conditions of ethylene ketal formation; the latter underwent in situ dimerization, cyclization, and rearrangement to give substituted indanols. The isopropenylphenol derived from 3,5-ditertbuty 1-4-hydroxyacetophenone did not dimerize but condensed with its precursor to yield a substituted diphenylpropanone. 3-nitro-, 3,5-dinitro-, and 3,5-dibromo-4-hydroxyacetophenones on the other hand reacted normally to give ethylene ketals in good yields.
- C-C Bond scission,
- Phenolic hydroxy participation,
- 4-hydroxyacetophenones,
- indanols,
- ethylene ketals
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