1,2-Dipolar-Cycloaddition of Benzylazide to (+)-Limonene: A Protection Cycle for the 8,9-Double Bond.

Article abstract of DOI:10.1016/0040-4039(95)00146-4

A method for protecting the 8.9-double bond of (+)-limonene (1) is described.The key step is the 1,3-dipolar-cycloaddition of benzylazide to 1, which affords N-benzyl-N-<9-(1-p-menthenylidene)>-amine (2) and N-benzyl-N-<8,9-(1-p-menthenylidene)>-amine (3).