Addition reaction of spiro orthoesters with electrophiles: A model reaction for the development of novel polyaddition accompanying ring‐opening isomerization

作者: Haruo Nishida , Fumio Sanda , Takeshi Endo , Takeshi Nakahara , Takayuki Ogata

DOI: 10.1002/(SICI)1099-0518(19991215)37:24<4502::AID-POLA6>3.0.CO;2-4

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摘要: The addition reaction of spiro orthoesters (SOEs) with electrophiles accompanying ring-opening isomerization was investigated as a model for polyaddition bifunctional SOEs electrophiles. Among several such carboxylic acids and anhydrides, acid halides showed particularly high reactivities to SOEs. An equimolar chlorides took place selectively, leading the corresponding 1: 1 adducts. seven-membered cyclic ether rings-1,4,6-trioxaspiro[5.6]undecane derivatives-showed higher than six- five-membered rings. accompanied zero shrinkage in volume.

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