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Cyclopropanes. XLI. Electron Transfer from Lithium Metal Surfaces to (±) and (−)‐( S )‐1‐Fluoro‐1‐methyl‐2,2‐diphenylcyclopropane
Author(s) -
Walborsky H. M.,
Powers E. J.
Publication year - 1981
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.198100041
Subject(s) - chemistry , cyclopropane , lithium (medication) , electron transfer , metal , ring (chemistry) , fluorine , lithium metal , photochemistry , medicinal chemistry , organic chemistry , medicine , endocrinology , electrode , electrolyte
The reaction of (I)‐1‐fluoro‐1‐methyl‐2,2‐diphenylcyclopropane ( 1 ) with lithium metal produced a variety of ring‐opened, as well as cyclopropane, products. Initial electron transfer from the lithium metal surface to 1 is to the phenyl ring of 1 rather than to the carbon‐fluorine bond. Using chiral 1 , the 1‐lithio‐1‐methyl‐2,2‐diphenylcyclopropane produced yielded, upon carbonation, the corresponding acid which was largely racemized. The mechanism of the electron transfer reaction is discussed.