Structure Correlation Study of Some Diels–Alder Cycloadducts of Anthracene

Article

<< Previous

Next >>

Contents Vol 62(5)

doi:10.1071/CH09050

Structure Correlation Study of Some Diels–Alder Cycloadducts of Anthracene

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

^A School of Chemistry and Bio-21 Institute, University of Melbourne, Parkville, Vic. 3010, Australia.
^B Corresponding author. Email: whitejm@unimelb.edu.au





	PDF (346 KB) $25



	Export Citation

Print

Australian Journal of Chemistry 62(5) 419–424 http://dx.doi.org/10.1071/CH09050
Submitted: 23 January 2009 Accepted: 16 February 2009 Published online: 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.