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29.5 Product Class 5: Hal/N and Hal/P Acetals

DOI: 10.1055/sos-SD-029-00297

Leroy, B.Science of Synthesis, (200729251.

General Introduction

α-Haloamino compounds are generally best depicted as an equilibrium between a covalent form and an iminium salt. However, for a substantial part of these compounds, the covalent form is predominant. This is the case when the lone pair on the nitrogen atom is either involved in conjugation (e.g., amides, heteroaromatic compounds) or forms a covalent bond (e.g., ammonium salts, nitro derivatives). Owing to the high CF bond energy, α-fluoroamino compounds are also essentially covalent. The structural and electronic properties of a molecule can also have an important impact on its degree of ionization, and it is often difficult to predict if the major form of α-haloamino compounds will be ionic or covalent. In this article, only products of a covalent nature are considered. Iminium salts are reviewed in detail in Science of Synthesis, Vol. 27 [Heteroatom Analogues of Aldehydes and Ketones (Section 27.827.8)]. Despite their potentially covalent character, α-haloamino compounds generally behave as iminium salts in their reactivity.[‌1‌,‌2‌] Therefore, they easily undergo addition of carbon or heteroatom nucleophiles. The preparation of Hal/N and Hal/P acetals has been discussed in a detailed review.[‌3‌]

References


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