On the claisen rearrangement of 1,4-diaryloxy-2-butynes

Ramakanth, S. ; Narayanan, K. ; Balasubramanian, K. K. (1984) On the claisen rearrangement of 1,4-diaryloxy-2-butynes Tetrahedron, 40 (21). pp. 4473-4481. 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)98822-2

Abstract

A proton nmr follow-up provided conclusive evidence for the involvement of two sequential Claisen rearrangements in the thermal rearrangement of 1,4-diaryloxy-2-butynes 1̲ to 11a-methylpterocarpans 3̲. A detailed study of the rearrangement of 1,4-diaryloxy-2-butynes 1̲ in polyethyleneglycol-200 (PEG-200), indicated a definite possibility of selective synthesis of either benzofuron (3,2-b )benzofuran 4̲ or benzofuro(2,3-b)benzofuran 5̲ by varying the temperature of the reaction alone.

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