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22.4.8.1.9.4 Method 4: Synthesis from Reagents with a Good Leaving Group

DOI: 10.1055/sos-SD-022-00489

Ostrowska, K.; Kolasa, A.Science of Synthesis, (200522461.

All methods that transform amidines into their various derivatives take advantage of either their electrophilic character at carbon or the nucleophilicity of the nitrogen. The former is used when formimidamide derivatives substituted at carbon with good leaving groups, such as sulfanyl (e.g., 258),[‌844‌] methylsulfanyl (e.g., 261, 262),[‌845‌,‌846‌] sulfonyl (e.g., 259, 264),[‌847‌,‌848‌] silyl group (e.g., 261, 265),[‌849‌] or phosphonate groups (e.g., 260),[‌850‌] react with carbon or hydrogen-based nucleophiles (Scheme 108). The exchange of the methylsulfanyl group by an aryl or a hetaryl group in a protected amidine allows this procedure to be carried out in the presence of aldehyde, ketone, or ester functional groups, e.g. formation of 263 (Scheme 108).[‌846‌]

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