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Addition of water to arylidenecyclopropanes: a highly efficient method for the preparation of gem-aryl disubstituted homoallylic alcohols

โœ Scribed by Amal I Siriwardana; Itaru Nakamura; Yoshinori Yamamoto

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
93 KB
Volume
44
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Arylidenecyclopropanes react with water in the presence of a catalytic amount of Cu(OTf) 2 to afford the corresponding gem-aryl disubstituted homoallylic alcohols in good to excellent yields.

๐Ÿ“œ SIMILAR VOLUMES

Addition of hydrogen halides to alkylide
Addition of hydrogen halides to alkylidenecyclopropanes: a highly efficient and stereoselective method for the preparation of homoallylic halides
โœ Amal I Siriwardana; Itaru Nakamura; Yoshinori Yamamoto ๐Ÿ“‚ Article ๐Ÿ“… 2003 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 152 KB

The reaction of alkylidenecyclopropanes with HCl or with HBr proceeds very smoothly at 120ยฐC to produce the corresponding homoallylic halides stereoselectively in good to excellent yields. For example, the reaction of (1-phenylbenzylidene)cyclopropane, (1-butylpentylidene)cyclopropane and octylidene

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โœ R.P. Volante ๐Ÿ“‚ Article ๐Ÿ“… 1981 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 176 KB

Various alcohols were converted to their corresponding thiolacetates by treatment with triphenylphosphine and diisopropyl azodicarboxylate in the presence of thiolacetlc acid. The overall conversion was both highly efficient (89-99X yields) and stereoselective (99.5% inversion).