Kinetics and mechanisms of nucleophilic displacements with heterocycles as leaving groups. 2. N-benzylpyridinium cations: rate variation with steric effects in the …

AR Katritzky, AM El-Mowafy, G Musumarra…

Index: Katritzky, Alan R.; El-Mowafy, Azzahra M.; Musumarra, Giuseppe; Sakizadeh, Kumars; Sana-Ullah, Choudhry; et al. Journal of Organic Chemistry, 1981 , vol. 46, # 19 p. 3823 - 3830

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Citation Number: 26

Abstract

31 32 33 for the preparation of 1, 5-diketones was applied (25+ 28-29). In two cases the cyclic enamine adduct intermediates 30 and 31 were isolated (Chart I). The piperidinobenzoxanthene 31 was found to undergo a retro-Michael reaction readily upon crystallization in ethanol, giving back 2-benzylidene-1-tetralone quantitatively. However, small amounts of acetic acid suppressed this fragmentation. The corresponding 1, ...