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Stereochemistry of 2‐methyl‐ and 2‐phenyl‐2‐adamantyl cations
Author(s) -
Herrmann Roland,
Kirmse Wolfgang
Publication year - 1995
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.1995199504100
Subject(s) - chemistry , diastereomer , acetone , stereoselectivity , aqueous solution , stereochemistry , medicinal chemistry , organic chemistry , catalysis
When both diastereomers of [5‐D]‐2‐methyl‐2‐adamantyl 2,4‐dinitrophenolate ( 18a ) and [5‐D]‐2‐phenyl‐2‐adamantyl 2,4‐dinitrophenolate ( 18b ) were solvolyzed in 40% aqueous acetone, 1:1 mixtures of ( E )‐ and (Z)‐[5‐D]‐2‐R‐adamantan‐2‐ols ( 19a, b ) were obtained. The stereoselectivity of secondary 2‐adamantyl cations, attributed to σ participation, is effectively suppressed by charge‐stabilizing groups at C‐2.