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Über Struktur und Stereoselektivität von 2‐Norbornen‐7‐yl‐Radikalen und ‐Carbenoiden
Author(s) -
Martínez Antonio García,
Barcina José Osío
Publication year - 1985
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.19851181035
Subject(s) - chemistry , stereoselectivity , methyllithium , carbenoid , stereochemistry , medicinal chemistry , radical , catalysis , organic chemistry , rhodium
On the Structure and Stereoselectivity of 2‐Norbornen‐7‐yl Radicals and Carbenoids Reduction of 7,7‐diiodonorbornene ( 1 ) with Grignard reagents proceeds via the 7‐iodo‐2‐norbornen‐7‐yl radical 2 . From the observed syn ‐stereoselectivity, the absence of π‐delocalization in 2 is inferred. This result agrees with the existence of an equilibrium mixture of two classical pyramidal structures ( 2a and 2b ), in which the syn ‐isomer 2a predominates. The reaction of 1 with methyllithium takes place with anti ‐stereoselectivity; this fact proves that the anti ‐carbenoid 4b‐M is more stable than the syn ‐isomer.