Prior to intercepting the diazomethane in situ, we speculated that by replacing the methyl group of acetophenone with extended alkyl substituents, we would be able to isolate non-gaseous diazoalkane by-products. Interestingly, upon the addition of propiophenone to the reaction mixture instead of acetophenone (See Figure .g.), product was not formed and the ketone remained unreacted. This result does not represent a limitation of our methodology because both substrates lead to the same product with a different by-product. Yet, the origin of this puzzling observation might shed light on the reaction mechanism. We postulated that the lack of propionate reactivity could be associated with one of the following challenges (Figure .i.): (a) imine formation might be prohibitive, (b) the tautomerization step to form enamine may be unfavorable, (c) bulkier substituents on the enamine might limit the approach of sulfonyl azides, and (d) the release of bulkier diazoalkanes may be less favorable than the release of diazomethane gas.