2 PATHWAYS FOR THE STEREOMUTATION OF 2-SUBSTITUTED 1-(TERT-BUTYLSULFINYL)NAPHTHALENES

Authors
BAKER RW KYASNOOR RV SARGENT MV
Citation
Rw. Baker et al., 2 PATHWAYS FOR THE STEREOMUTATION OF 2-SUBSTITUTED 1-(TERT-BUTYLSULFINYL)NAPHTHALENES, Perkin transactions. 2, (6), 1998, pp. 1333-1337
Citations number
17
Categorie Soggetti
Chemistry Physical","Chemistry Inorganic & Nuclear
Journal title
Perkin transactions. 2 → ACNP
ISSN journal
03009580
Issue
6
Year of publication
1998
Pages
1333 - 1337
Database
ISI
SICI code
0300-9580(1998):6<1333:2PFTSO>2.0.ZU;2-#
Abstract
The synthesis of a number of 2-substituted 1-(tert-butylsulfinyl)napht halenes is described and the free energies of activation (Delta G doub le dagger = 50.0-80.7 kJ mol(-1)) far their stereomutation about the S -Ar bonds have been determined, It is shown that two pathways operate for this process. For the smaller 2-substituents (F, OMe, CO2Pt), the tert-butyl group passes over the 2-position, and for larger substituen ts (Cl, Me, Pr-i) it passes over the 8-position of the naphthalene rin g.