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25.6.6.4.1 Variation 1: Using Dimethylformamide and Pyrophosphoryl Chloride

DOI: 10.1055/sos-SD-025-00443

Schall, A.; Reiser, O.Science of Synthesis, (200725618.

A seemingly small variation that can have quite a large effect is the use of pyrophosphoryl chloride instead of phosphoryl chloride, which precludes the formation of a chloroiminium salt 11 but rather leads to the formation of the iminium salt 12 (Scheme 8).[‌15‌] The latter is a more reactive electrophile often giving better yields, for example in the synthesis of benzaldehyde 13. In addition, due to its increased steric bulk, better regioselectivity, favoring sterically less-crowded positions for the introduction of a formyl group, is observed.

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