183200-34-2Relevant academic research and scientific papers
A method for synthesis of homoallylic bromide
Qi, Wenke,Wang, Peipei,Fan, Liyuan,Zhang, Songlin
, p. 5918 - 5924 (2013/07/26)
Cyclopropyl Grignard reagents react with carbonyl compounds in the presence of diethyl phosphite to give homoallylic bromides. The reaction is effectively carried out under mild conditions in a one-pot fashion with moderate to good yields.
Studies on the mechanism, selectivity, and synthetic utility of lactone reduction using SmI2 and H2O
Parmar, Dixit,Duffy, Lorna A.,Sadasivam, Dhandapani V.,Matsubara, Hiroshi,Bradley, Paul A.,Flowers II, Robert A.,Procter, David J.
supporting information; experimental part, p. 15467 - 15473 (2010/02/16)
Although simple aliphatic esters and lactones have long been thought to lie outside the reducing range of SmI2, activation of the lanthanide reagent by H2O allows some of these substrates to be manipulated in an unprecedented fashion. For example, the SmI2-H2O reducing system shows complete selectivity for the reduction of 6-membered lactones over other classes of lactones and esters. The kinetics of reduction has been studied using stopped-flow spectrophotometry. Experimental and computational studies suggest that the origin of the selectivity lies in the initial electron-transfer to the lactone carbonyl. The radical intermediates formed during lactone reduction with SmI2-H2O can be exploited in cyclizations to give cyclic ketone (or ketal) products with high diastereoselectivity. The cyclizations constitute the first examples of ester-alkene radical cyclizations in which the ester carbonyl acts as an acyl radical equivalent.
A convenient one-pot synthesis of homoallylic halides and 1,3-butadienes
Wong, Ken-Tsung,Hung, Ying-Yueh
, p. 8033 - 8036 (2007/10/03)
An efficient one-pot synthetic pathway for the preparation of homoallylic halides by in situ generated MgBrCl-promoted ring opening of cyclopropylcarbinyl acetates has been established. An easily accessible one-pot synthetic protocol of 1,3-butadienes by the elimination of hydrogen halides from the resulting homoallylic halides in the presence of an excess amount of strong base has also been developed.
Regiospecific Nucleophilic Substitution in Cyclopropylcarbinols. Stereospecific Opening of the Cyclopropane Ring
Matveeva,Kvasha,Kurts
, p. 17 - 20 (2007/10/03)
Reactions of cyclopropylcarbinols with hydrobromic acid and the triphenylphosphine-tetrabromomethane complex at 0°C result in stereospecific opening of the cyclopropane ring with formation of trans-homoallyl bromides.
