Devarajan, Krishnan ; Devaraj, Somasundaram ; Balasubramanian, Kalpattu K ; Bhagavathy, Shanmugasundaram (2015) An Unexpected Thermal [1,3]-[1,3]-paraRearrangement of Chromone-3-ylmethyl Aryl Ethers: Mechanism and Application of the Intercepted [1,3]-Rearranged Intermediates to the Synthesis ofcis-Homopterocarpans Chemistry Letters, 44 (4). pp. 551-553. ISSN 0366-7022
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Official URL: http://doi.org/10.1246/cl.141162
Related URL: http://dx.doi.org/10.1246/cl.141162
Abstract
Chromone-3-ylmethyl aryl ethers with unsubstituted ortho-positions have been found to undergo a novel domino [1,3]-[1,3]-rearrangement to give 4′-hydroxyhomoisoflavones under thermal conditions while the para-substituted ethers lead to 2′-hydroxyhomoisoflavones involving an O- to C-[1,3]-migration, instead of the expected Claisen rearrangement. A few cis-homopterocarpans have been synthesized using the 2′-hydroxyhomoisoflavones obtained from the thermal [1,3]-rearrangement of chromene-3-ylmethyl aryl ethers.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to The Chemical Society of Japan. |
| ID Code: | 128951 |
| Deposited On: | 07 Nov 2022 05:56 |
| Last Modified: | 07 Nov 2022 05:56 |
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