Comparative study of the reactions ofn-BuMgBr andn-BuLi with cyclododecanone

The composition of the products obtained in the reactions ofn-BuMgBr andn-BuLi with cyclodecanone (1) has revealed that1 exhibits the properties of a sterically hindered ketone. The highest yield of 1-butylcyclododecanol (2) was achieved with the use ofn-BuMgBr, but in this case cyclododecanol was also formed, whereas the use ofn-BuLi led to the tertiary alcohol more distinctly. Dehydration of alcohol2 resulted in a mixture of three olefins containing up to 90 % ofE- andZ- isomers of 1-butylcyclododecene.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 907–909, May, 1993.