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A Radical Roundabout for an Unprecedented Tandem Reaction Including a Homolytic Substitution with a Titanium‐Oxygen Bond
Author(s) -
Gansäuer Andreas,
Rinker Björn,
NdeneSchiffer Noëllie,
Pierobon Marianna,
Grimme Stefan,
Gerenkamp Mareike,
MückLichtenfeld Christian
Publication year - 2004
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/ejoc.200400001
Subject(s) - homolysis , chemistry , radical , tandem , alkyl , sn2 reaction , substitution reaction , free radical reaction , organic chemistry , photochemistry , composite material , materials science
Conceptually novel homolytic substitutions (S H 2) of ClCp 2 Ti−O bonds with benzylic, secondary and tertiary alkyl radicals are described. The intermediates and crucial transition structures were studied by DFT methods. The resulting atom economical radical tandem reaction can be utilized for the synthesis of structurally complex tetrahydrofurans from simple starting materials and is therefore of interest for natural product synthesis. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)