The Reaction of Cyclopropyl Ketones with Acetyl Methanesulfonate. An efficient ring opening under neutral conditions with regiospecific enol acetate formation and stereo‐controlled nucleophilic addition. Preliminary communication | Zendy

Demuth Martin | Zendy; Raghavan Palaykotai R. | Zendy

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The Reaction of Cyclopropyl Ketones with Acetyl Methanesulfonate. An efficient ring opening under neutral conditions with regiospecific enol acetate formation and stereo‐controlled nucleophilic addition. Preliminary communication

Author(s) -

Demuth Martin,

Raghavan Palaykotai R.

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620730

Subject(s) - chemistry , nucleophile , enol , stereoselectivity , yield (engineering) , ring (chemistry) , medicinal chemistry , nucleophilic addition , stereochemistry , organic chemistry , catalysis , metallurgy , materials science

Cyclopropyl ketones are readily cleaved under neutral conditions at room temperature by the combined action of acetyl methanesulfonate and nucleophiles such as Br − , I − , and MsO − . The high‐yield reaction involves regiospecific enol acetate formation with a stereoselectivity of nucleophile addition which is compatible with an S N 2‐type opening of the cyclopropyl ring.

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