- Oxidizing polymers: A polymer-supported, recyclable hypervalent iodine(V) reagent for the efficient conversion of alcohols, carbonyl compounds, and unsaturated carbamates in solution
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The oxidation of various alcohols and cyclization of an olefinic carbamate succeeds with the first polymer-supported iodine(v) reagent (see scheme). The novel oxidizing polymer oxidizes sensitive and complex alcohols, including protected amino alcohols, efficiency in good excellent yields. In addition, the α,β-dehydration of a ketone is demonstrated.
- Sorg,Mengel,Jung,Rademann
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p. 4395 - 4397
(2007/10/03)
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- Reaction of isopulegol and similar alcohols with sulfuryl chloride
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The reaction of isopulegol with sulfuryl chloride (or chlorine) gives two types of products: on one hand 8-chlorocitronellal and 6-chloroisocitronellal both issued from a fragmentation pathway and, on the other hand 10-chloroisopulegol resulting from an allylic chlorination.The first process, the radical nature of which is demonstrated, is clearly favored by elevated temperatures while the second one is exclusive at 0 deg C.Homologous compounds such as p-mentha-1,8-dien-5-ols, 3-phenylisopulegol and isopulegone dioxolane give rise to one or both of these processes. --- Key Words: allylic chlorination / radical fragmentation
- Bulliard, M.,Balme, G.,Monteiro, N.,Gore, J.
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p. 222 - 231
(2007/10/02)
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- FRAGMENTATION OF ISOPULEGOL BY A RADICAL PROCESS
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The reaction of isopulegol with sulfuryl chloride leads in certain conditions to a mixture of 8-chloro citronellal and 6-chloro isocitronellal.The radical character of this fragmentation is supported by the result of two reactions known to proceed via an alkoxy radical.
- Bulliard, Michel,Balme, Genevieve,Gore, Jacques
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p. 2213 - 2216
(2007/10/02)
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- OXIDATION OF ALCOHOLS TO ALDEHYDES AND KETONES via aci-NITROESTERS OF ETHYL NITROACETATE UNDER NEUTRAL CONDITIONS
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The reaction of alcohols with ethyl nitroacetate, diethyl azodicarboxylate, and triphenylphosphine gave the corresponding aldehydes or ketones in 52-85percent yields.
- Mitsunobu, Oyo,Yoshida, Naoyuki
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p. 2295 - 2296
(2007/10/02)
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