References
- Williams , D R , Robinson , L A , Amato , G S and Osterhout , M H . 1992 . J Org Chem , 57 : 3740 For recent examples see
- Page , P C B , Graham , A E and Park , B K . 1992 . Tetrahedron Letters , 48 : 7265 and references therein.
- Unpublished observations; these laboratories
- Taylor , H M and Hauser , C R . Org Syn Coll , Vol 5 437
- At best a 3:1 mixture in favour of C-alkylation was obtained.
- Anders , E , Opitz , A and Bauer , W . 1991 . Synthesis , : 1221 The alkylation C versus N of similar anions has been examined:
- Fieser and Fieser . ‘Reagents for Organic Synthesis’ , Vol 1 993
- Fuller , M W and Schubert , W M . 1963 . JACS , 85 : 108 The only useful preparation is given by
- Meyers , A I and Campbell , A L . 1979 . Tetrahedron Letters , : 4155
- Meyers , A I , Campbell , A L , Abatjoglou , A G and Eliel , E L . 1979 . Tetrahedron Letters , : 4159
- I am grateful to Prof R A Raphael for suggesting this method of hydrolysis.
- Other pyridine aldehydes were examined briefly. The acetal of pyridine-3-aldehyde was not expected to behave analogously. That of pyridine-2-aldehyde, although apparently forming an anion on base treatment at -780C gave only intractable mixtures of products when reacted with electrophiles.