Structure Correlation Study of Some Diels–Alder Cycloadducts of Anthracene

Yit W. Goh; Jonathan M. White

doi:10.1071/CH09050

RESEARCH ARTICLE

Previous Next Contents Vol 62(5)

Structure Correlation Study of Some Diels–Alder Cycloadducts of Anthracene

Yit W. Goh ^A and Jonathan M. White ^A ^B

+ Author Affiliations

- Author Affiliations

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

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

Australian Journal of Chemistry 62(5) 419-424 https://doi.org/10.1071/CH09050
Submitted: 23 January 2009 Accepted: 16 February 2009 Published: 15 May 2009

Abstract

Crystal structures of some Diels–Alder cycloadducts of anthracene and a variety of dienophiles reveal structural effects consistent with the manifestation of the early stages of the retro Diels–Alder reaction in the ground state structure. The symmetrical cycloadducts 3 and 4 reveal a qualitative relationship between structure and reactivity, whereas the cycloadducts of 9-methoxyanthracene show structural effects suggestive of the early stages of an asynchronous retro Diels–Alder reaction.

Acknowledgements

Our gratitude goes to the University of Melbourne for MIRS and MIFRS scholarships, and Albert Shimmin Fund award to Goh Yit Wooi.

References

Structure Correlation Study of Some Diels–Alder Cycloadducts of Anthracene

Abstract

Acknowledgements

Subscriber Login