Further Information
Literature
Related Reactions
Cope Elimination
Ester Pyrolysis
Hofmann Elimination
Saytzeff's Rule
Hofmann's Rule
Hofmann's Rule implies that steric effects have the greatest influence
on the outcome of the Hofmann
or similar eliminations. The loss of the β-hydrogen occurs preferably
from the most unhindered (least substituted) position [-CH3 >
-CH2-R > -CH(R2)]. The product alkene with fewer
substitutents will predominate.
Ester Pyrolysis also obeys this preference, and the Hofmann Rule is
generally followed whenever a reaction passes through a cyclic
transition state.
Hofmann's Rule is valid for all intramolecular eliminations and for the Hofmann Elimination. Most bimolecular eliminations will follow Saytzeff's Rule.
Recent Literature
Triphosgene and DMAP as Mild Reagents for Chemoselective Dehydration of Tertiary Alcohols
M. O. Ganiu, A. H. Cleveland, J. L. Paul. R. Kartika, Org. Lett., 2019, 21, 5611-5615.