Herein presented is a review of the reactivity and synthetic utility of ortho-quinone methides and ortho-quinone methide imines. These versatile intermediates have received significant attention in the literature and new methods for their preparation and reaction as well as recent applications in total synthesis are discussed. 1 Introduction 2 Conjugate Addition Reactions 3 Concerted Cycloaddition Reactions 4 Stepwise Addition Reactions 5 Applications in Total Synthesis 6 Conclusion