Russian Chemical Bulletin

, Volume 46, Issue 7, pp 1269–1271 | Cite as

Reinvestigation of the Nazarov cyclization of 1-(3-hydroxypropynyl)cyclododecan-1-ol to bicyclo[10.3.0]pentadec-1(12)-en-13-one

  • L. I. Zakharkin
  • V. V. Guseva
  • P. V. Petrovskii
Organic Chemistry


Reinvestigation of the acid-catalyzed cyclization of 1-(3-hydroxypropynyl)cyclododecan-1-ol under the conditions of the Nazarov reaction demonstrated that this conversion yields two isomeric bicyclic ketones, namely, bicyclo[10.3.0]pentadec-1(12)-en-13-one and bicyclo[10.3.0]pentadec-1-en-3-one. The latter compound is thermodynamically less stable.

Key words

1-(3-hydroxypropynyl)cyclododecan-1-ol acid-catalyzed cyclization Nazarov reaction unsaturated bicyclic ketones 


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Copyright information

© Plenum Publishing Corporation 1997

Authors and Affiliations

  • L. I. Zakharkin
    • 1
  • V. V. Guseva
    • 1
  • P. V. Petrovskii
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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