Thyagarajan, B. S. ; Balasubramanian, K. K. ; Bhima Rao, R. (1967) Studies in claisen rearrangement-IV : 4-phenoxymethyl-Δ3-chromene as an intermediate in the formation of 6H-benzofuro(3·2-c)[1]-(11a,6a-dihydro-11a-methyl)benzopyran Tetrahedron, 23 (4). pp. 1893-1899. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...
Related URL: http://dx.doi.org/10.1016/S0040-4020(01)82591-6
Abstract
Of two conceivable mechanistic pathways in the conversion of 1,4-diaryloxy-2-butynes to benzofurobenzopyrans, one is eliminated and the other validated. Whereas 2-methyl-3-phenoxymethylbenzofuran is resistant to Claisen rearrangement, 4-phenoxymethyl-Δ3-chromene undergoes such a rearrangement with concomitant ring closure to the benzofurobenzopyran (VIII). The related system viz. 4-phenoxymethylcoumarin showed no propensity for similar rearrangement.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 3780 |
| Deposited On: | 18 Oct 2010 09:48 |
| Last Modified: | 13 May 2011 08:58 |
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