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2‐Oxabicyclo[3.2.1]oct‐7‐yl‐Kationen
Author(s) -
Kirmse Wolfgang,
Mönch Dietmar
Publication year - 1992
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19921250541
Subject(s) - chemistry , bicyclic molecule , 2 norbornyl cation , medicinal chemistry , stereochemistry
2‐Oxabicyclo[3.2.1]oct‐7‐yl Cations 2‐Oxabicyclo[3.2.1]octan‐7‐one ( 10 ) was prepared in five steps, starting from 3‐cyclopenten‐1‐ol ( 5 ). The tosylhydrazone 11 , derived from 10 , was photolyzed in 0.5 N NaOD/D 2 O to give >99% of 2‐oxabicyclo[3.2.1]octan‐ exo ‐7‐ol ( 9 ) with equal distribution of D at C‐1 and C‐7. In contrast to the parent 6‐bicyclo[3.2.1]octyl cation ( 1 ), the oxa analog 14 exhibits the same symmetry as was observed with the 6‐oxa‐2‐norbornyl cation ( 13 ). The conformational effects that are evident in 1 are overruled by strong n participation.