Tetrahedron p. 2183 - 2187 (1984)
Update date:2022-08-05
Topics:
Adinolfi, Matteo
Barone, Gaspare
Lanzetta, Rosa
Laonigro, Guglielmo
Mangoni, Lorenzo
Parrilli, Michelangelo
The addition of ICl and IBr to 1-methyl-4-t-butylcyclohexene has been investigated in chloroform and carbon tetrachloride and the distribution of the produced trans-iodohalogenides has been determined by NMR spectroscopy.The stereoselectivity of the addition was found to be determined by both the reversible electrophilic first step and the nucleophilic second step.The higher stereoselectivity of the addition of IBr is interpreted on the basis of the higher softness of bromide ion with respect to chloride ion.
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