29583-33-3Relevant articles and documents
Dual behavior of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions
Jereb, Marjan,Vra?i?, Dejan,Zupan, Marko
scheme or table, p. 2347 - 2352 (2009/09/06)
The dual behavior phenomenon of alcohols in iodine-catalyzed esterification under solvent-free reaction conditions (SFRCs) is described; the governing factor is the stability of the carbonium ion generated from the alcohol; high concentration reaction conditions (HCRCs) or dilute solutions are much less suitable. In the case of benzylic alcohols, loss of optical activity was noted, whereas alkyl alcohols furnished a product with retention of stereochemistry.
The Protonated Cyclopropane Route to Bicyclic Cations
Kirmse, Wolfgang,Streu, Joachim
, p. 515 - 521 (2007/10/02)
The protolytic cleavage of tricyclo2,6>hexane (3), tricyclo2,7>heptane (10), methyltricyclo2,7>heptanes (26), tricyclo2,8>octane (53), and tricyclo2,7>octane (58) in acetic acid and in aqueous dioxane has been investigated.Protonation occurred at a specific site (3, 36b,d, 58) or competitively at two sites (10, 26c, 53), depending on the stability of the incipient carbocations.Product distributions and label redistributions, where applicable, were in good to excellent agreement with previous solvolytic studies.We conclude that the protonated cyclopropane and ? routes are equivalent in generating bridged carbocations.Edge-protonated cyclopropanes play a minor role, if any, in product formation.Stereoselectivity appears to be an intrinsic property of the cationic intermediates, largely independent of the specific orientation of their counterions.