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Opening of Diaryl Epoxides: ortho ‐Fluorophenyl and 2‐Pyridyl Epoxides
Author(s) -
SolladiéCavallo Arlette,
Lupattelli Paolo,
Marsol Claire,
Isarno Thomas,
Bonini Carlo,
Caruso Leonilde,
Maiorella Angelica
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:8<1439::aid-ejoc1439>3.0.co;2-0
Subject(s) - chemistry , epoxide , regioselectivity , organic chemistry , catalysis
Opening of epoxides with LiAlH 4 , MgBr 2 ·2OEt 2 (solution in Et 2 O), MgBr 2 ·OEt 2 (suspension in Et 2 O), and NaBr/Amberlyst‐15 has been studied. While 2‐pyridyl epoxide 1 opens with complete regioselectivity, ortho ‐fluorophenyl epoxide 2 does not, but affords mixtures. Moreover, while the anti isomer (100−80%) is in all cases the major product with epoxide 1 , epoxide 2 affords the anti isomer as major product with MgBr 2 and the syn isomer as major product with NaBr/Amberlyst‐15. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)