Ring selectivity: Successive ring expansion of two benzocyclobutenes for divergent access to angular and linear benzanthraquinones

Angewandte Chemie - International Edition

Volumn 47, Issue 12, 2008, Pages 2248-2252

  Suzuki, Takeaki ^a   Hamura, Toshiyuki ^a   Suzuki, Keisuke ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Pericyclic reactions; Polyaromatic compounds; Ring expansion; Ring selectivity; Strained molecules

Indexed keywords

BUTENES; ETHYLENE;

PERICYCLIC REACTIONS; POLYAROMATIC COMPOUNDS; RING EXPANSION; RING SELECTIVITY; STRAINED MOLECULES;

THERMAL EXPANSION;

BENZ[A]ANTHRACENE DERIVATIVE; BENZOCYCLOBUTENE; POLYCYCLIC HYDROCARBON; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

BENZ(A)ANTHRACENES; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS;

EID: 41049107458     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705630     Document Type: Article

References (49)

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29. All new compounds were characterized fully by spectroscopy and combustion analysis.
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37. Products cis-11 and trans-11 were obtained as mixtures of diastereomers in ratios of 1:3.2 and 1:1.4, respectively. The diastereomers were separated by recycling preparative HPLC for structure assignment; see the Supporting Information.
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48. The reaction of 15 gave cis-16 as the only isolable product; thus, the reaction proceeded with high cis selectivity.
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