Beilstein J. Org. Chem.2011,7, 1215–1218, doi:10.3762/bjoc.7.141
Victor Snieckus Department of Chemistry, Queen's University, Kingston, Ontario, K7L 3N6, Canada 10.3762/bjoc.7.141 The title of this Thematic Series brings to the minds of most organic chemists the beautifully logical aromatic electrophilic substitution (SEAr) [1][2][3][4][5] and, to a lesser
heteroaromatics [15][16][17]. While comparison with SEAr and SNAr should never be denied, the DoM approach offers incontestable ortho regioselectivity, mild conditions, and perhaps most significantly, broad post-DoM synthetic potential. As a result, it has been called upon, with increasing favor and frequency, by
exchange) chemistry, alternative and competitive combinational metal amide bases are rapidly appearing [47][48]. The first successful glimpses of the much sought after complementary, cleaner, regiodefined, and milder procedures to ortho, para versus meta SEAr reactions are being seen in Cu-catalyzed meta
Beilstein J. Org. Chem.2009,5, No. 9, doi:10.3762/bjoc.5.9
of enantiomerically pure 4-hydroxy[2.2]paracyclophane or application of our own sulfoxide-metal exchange protocol [31] would permit enantiospecific variants of either route, but neither has been reported. An elegant entry to a variety of racemic alkyl sulfides and sulfoxides by an SEAr reaction
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Graphical Abstract
Figure 1:
[2.2]Paracyclophane (1) showing standard numbering and [2.2]paracyclophane-4-thiol (2).