Electrocyclic Ring-Opening of 6,6-Dichlorobicyclo[3.1.0]-hexanes and Trapping of the Resulting π-Allyl Cations by C-1 Tethered Hydroxyamine Derivatives: Formation of 2-Oxa-1-azaspiro[4.5]decan-3-ones
Jiri Mikusek A , Jas S. Ward A and Martin G. Banwell A B
+ Author Affiliations
- Author Affiliations
A Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 2601, Australia.
B Corresponding author. Email: Martin.Banwell@anu.edu.au
Australian Journal of Chemistry 72(6) 434-439 https://doi.org/10.1071/CH19010
Submitted: 7 January 2019 Accepted: 12 February 2019 Published: 14 March 2019
Abstract
The C-1 substituted 6,6-dichlorobicyclo[3.1.0]hexanes 1a–c have been prepared and shown to undergo electrocyclic ring-opening to give the corresponding π-allyl cations 2 that cyclise to afford the spirocyclic products 3b–d, each of which has been subjected to single-crystal X-ray analysis.
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