Syntheses of substituted 1,4-naphthoquinones by Diels–Alder addition of methoxycyclohexadienes to substituted 1,4-benzoquinones

Giles, R.G.F. and Roos, G.H.P. (1976) Syntheses of substituted 1,4-naphthoquinones by Diels–Alder addition of methoxycyclohexadienes to substituted 1,4-benzoquinones. Journal of the Chemical Society, Perkin Transactions 1 (19). pp. 2057-2060.

Abstract

Additions of 1-methoxycyclohexa-1,3-diene to 2-methoxy-3-methyl-1,4-benzoquinone and to chloro-1,4-benzoquinone give Diels–Alder adducts which are coverted in high yield into substituted juglone methyl ethers. Reactions between 1-methoxy-3-methylcyclohexa-1,3-diene and methoxy-1,4-benzoquinone follow a similar course. Addition of 1,3-dimethoxycyclohexa-1,3-diene to chloro- or methoxy-benzoquinone affords a dihydrodibenzofuran rather than a Diels–Alder adduct.

Item Type:	Journal Article
Publisher:	Royal Society of Chemistry
Copyright:	© 1976 Royal Society of Chemistry
URI:	http://researchrepository.murdoch.edu.au/id/eprint/35594

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