Reaction of 2a,8b-Dihydrobenzo[b]cyclobute[d]pyran-3-ones with Dimethylsulfoxonium Methylide

Using dimethylsulfoxonium methylide as the methylene transfer reagent, 2a,8b-dihydrobenzo[b]cyclobute[d]pyran-3-ones were converted into 2,2′-biphenol derivatives as major products and dihydrodibenzofurans as minor products. The reaction mechanism was extrapolated from a deuteration experiment with...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2016/07/01, Vol.64(7), pp.1056-1061
Hauptverfasser:	Tanaka, Toru, Nagahama, Masaki, Yadav, Navnath Dnyanoba, Iwasaki, Hiroki, Ozeki, Minoru, Kojima, Naoto, Yamashita, Masayuki
Format:	Artikel
Sprache:	eng
Schlagworte:	2,2′-biphenol Cyclobutanes - chemistry cyclobutene Dibenzofurans - chemical synthesis Dibenzofurans - chemistry Molecular Structure Phenols - chemical synthesis Phenols - chemistry ring opening Sulfonium Compounds - chemistry ylide
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Beschreibung
Zusammenfassung:	Using dimethylsulfoxonium methylide as the methylene transfer reagent, 2a,8b-dihydrobenzo[b]cyclobute[d]pyran-3-ones were converted into 2,2′-biphenol derivatives as major products and dihydrodibenzofurans as minor products. The reaction mechanism was extrapolated from a deuteration experiment with CD2=S(O)(CD3)2.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.c16-00303