Russian Chemical Bulletin

, Volume 42, Issue 5, pp 861–863 | Cite as

Some transformations of 2-benzylcyclododecanones prepared by alkylation of cyclododecanone with benzyl halides under conditions of phase transfer catalysis

  • L. I. Zakharkin
  • I. M. Churilova
  • A. P. Pryanishnikov
Organic Chemistry
  • 24 Downloads

Abstract

Cyclododecanone is readily alkylated with benzyl halides (ArCH2X) to give 2-benzylcyclododecanones under conditions of phase transfer catalysis. Under the action of polyphosphoric acid 2-benzylcyclododecanone undergoes cyclization to give 1,2,3,4,5,6,7, 8,9,10-decahydrocyclododeca[b]indene. It also reacts with NOCl to give 12-hydroxyimino-2-benzylcyclododecanone, which enters the Beckmann rearrangement to afford 2-benzyl-1,12-dodecandioic acid.

Key words

cyclododecanone 2-benzylcyclododecanone 1,2,3,4,5,6,7,8,9,10-decahydrocyclododeca[b]indene 12-hydroxyimino-2-benzylcyclododecanone 2-benzyl-1,12-dodecandioic acid 12-hydroxyimino-2-(1-n-hexyl)cyclododecanone 2-(1-n-hexyl)-1,12-dodecandioic acid 1-acetoxy-2-benzylcyclododecene 

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Copyright information

© Plenum Publishing Corporation 1994

Authors and Affiliations

  • L. I. Zakharkin
    • 1
  • I. M. Churilova
    • 1
  • A. P. Pryanishnikov
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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