The reaction of 1-chloro-2-methyl-2-propenyllithium with a selection of organolithiums. The development and synthetic utility of novel base/nucleophile combinations

Article abstract of DOI:10.1016/0022-328X(93)83391-8

The title compound was generated by and reacted with (1) a series of reagents which have basic as well as nucleophilic properties and (2) a series of base/nucleophile combinations.Product yields of the isobutenyl derivative were generally low to very good, and the best results (89percent) were obtained by using a 1:2 ratio (3 equiv total) of ⁿBuLi:LiPPh2.Synthetic utility of the reaction is optimized as it approaches a situation in which the base/nucleophile combination is composed of one compound which is both a strong base and a poor nucleophile and another compound which is both a weak base and a good nucleophile.