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Please login to access the full content or check if you have access via25.6.6.4.1 Variation 1: Using Dimethylformamide and Pyrophosphoryl Chloride
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Schall, A.; Reiser, O., Science of Synthesis, (2007) 25, 618.
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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References
| [15] | Meeeee, M. M.; Meeee, M. M.; Meeeee, M.; Meeeeeeee, M. M., Meeeeeeeeee, (8888) 88, 8888. |
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