Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Ketene and Its Derivatives. LIII. Reaction of Diketene with Diazoacetophenone and Ethyl Diazoacetate
TETSUZO KATONOBUYA KATAGIRI
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1973 年 21 巻 4 号 p. 729-735

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Diketene reacted with diazoacetophenone (Ia) to give two isomeric spiro compounds, 2-(trans-2-benzoyl-1-hydroxycyclopropane)-acetic acid β-lactone (IIa) and 2-(cis-2-benzoyl-1-hydroxycyclopropane)-acetic acid β-lacton.e (IIa'). Similarly, p-methoxy-α-diazoacetophenone (Ib) was transformed to 2-[trans-2-(p-methoxybenzoyl)-1-hydroxycyclopropane]-acetic acid β-lactone (IIb) and 2-[cis-2-(p-methoxybenzoy1)-1-hydroxycyclopropane]-ace tic acid β-lactone (IIb'). Reaction of diketene with ethyl diazoacetate (Ic) gave furanone derivatives, 2, 5-dihydro-2-ethoxycarbonyl-3-methylfuran-5-one (VII) and 2, 5-dihydro-4-ethoxycarbonyl-methylfuran-2-one (VIII), together with 2-(trans-2-ethoxycarbony1-1-hydroxycyclo-propane) acetic acid β-lactone (IIc).
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© The Pharmaceutical Society of Japan
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