引用本文:
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.
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.
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.
Further Report on A Novel Scission of Alkyl Carbonyl C-C Bond by Substituted 4-Hydroxyacetophenones
摘要:
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.
English
Further Report on A Novel Scission of Alkyl Carbonyl C-C Bond by Substituted 4-Hydroxyacetophenones
Abstract:
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.
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Key words:
- C-C Bond scission
- / Phenolic hydroxy participation
- / 4-hydroxyacetophenones
- / indanols
- / ethylene ketals
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