X-ray Structural Analysis for the Prediction on the Nature of the Retro Diels–Alder Pathway: Concerted or Stepwise. Structural Studies on Nitrosobenzene Cycloadducts

Jesse Roth-Barton; Jonathan M. White

doi:10.1071/CH09349

RESEARCH ARTICLE

Previous Contents Vol 62(12)

X-ray Structural Analysis for the Prediction on the Nature of the Retro Diels–Alder Pathway: Concerted or Stepwise. Structural Studies on Nitrosobenzene Cycloadducts

Jesse Roth-Barton ^A and Jonathan M. White ^A ^B

+ Author Affiliations

- Author Affiliations

^A School of Chemistry and Bio-21 Institute, University of Melbourne, Vic. 3010, Australia.

^B Corresponding author. Email: whitejm@unimelb.edu.au

Australian Journal of Chemistry 62(12) 1695-1698 https://doi.org/10.1071/CH09349
Submitted: 19 June 2009 Accepted: 25 August 2009 Published: 10 December 2009

Abstract

Crystal structures of nitrosobenzene cycloadducts 5–7 reveal structural effects consistent with the early stages of the retro Diels–Alder fragmentation. There is a clear differentiation between the structure parameters of cycloadduct 5, which reacts by a concerted synchronous pathway and that of cycloadduct 6, which must react by a two-step pathway. Based on these data, cycloadduct 7 is predicted to react by a highly asynchronous or two-step pathway.

References

X-ray Structural Analysis for the Prediction on the Nature of the Retro Diels–Alder Pathway: Concerted or Stepwise. Structural Studies on Nitrosobenzene Cycloadducts

Abstract

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