ALKYLATION OF TRICARBONYLCHROMIUM-STABILIZED BENZYLIC ANIONS OF 3-(DIPROPYLAMINO)CHROMAN

Authors
BRISANDER M CALDIROLA P JOHANSSON AM HACKSELL U
Citation
M. Brisander et al., ALKYLATION OF TRICARBONYLCHROMIUM-STABILIZED BENZYLIC ANIONS OF 3-(DIPROPYLAMINO)CHROMAN, Journal of organic chemistry, 63(16), 1998, pp. 5362-5367
Citations number
30
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
16
Year of publication
1998
Pages
5362 - 5367
Database
ISI
SICI code
0022-3263(1998)63:16<5362:AOTBAO>2.0.ZU;2-S
Abstract
Tricarbonylchromium complexes of racemic and resolved 3-(dipropylamino )chromans were prepared. Benzylic alkylation of the complexes provided access to 4-alkylated derivatives. Alkylations of the endo complex ga ve only the expected trans products. Unexpectedly, the exo complex pre dominantly (with methyl iodide) or almost exclusively (with allyl and benzyl bromide) produced the trans derivatives. Steric effects and the nature of the electrophiles appear to direct the outcome of the alkyl ations.