A new synthesis of N-arylazetidines

Deady, Leslie W.; Topsom, R. D.; Hutchinson, R. E. J.; Vaughan, J.; Wright, G. J.

doi:10.1016/s0040-4039(01)99048-3

Cited by 7 publications

(3 citation statements)

References 7 publications

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“…1N4 was synthesized by reacting 1-fluoronaphthalene (Aldrich) with azetidine (Merck), following the procedure used for P4C . 1N5 was made from naphthalene-1-yl-(4-phenoxybutyl)amine and AlCl 3 . This amine resulted from a reaction between 1AN (Merck) and 4-methoxybutylbromide .…”

Section: Methodsmentioning

confidence: 99%

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Internal Conversion in 1-Aminonaphthalenes. Influence of Amino Twist Angle

et al. 1999

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With the 1-aminonaphthalenes 1N5 and 1DMAN a fast radiationless process occurs in n-hexane, diethyl ether, and acetonitrile, which is shown to be internal conversion (IC). The IC reaction is slower with 1N4 and much less efficient with 1MAN and 1AN. This IC process is thermally activated and slows down with increasing solvent polarity, due to a larger IC activation energy. In the ground state S0, the amino twist angle θ relative to the naphthalene plane increases in the order 1MAN, 1AN, 1N4, 1N5, 1DMAN, as derived from absorption and fluorescence spectra, 1H NMR spectra, ground-state dipole moments, and ab initio calculations. For the five 1-aminonaphthalenes in the equilibrated S1 state, the twist angle and the radiative rate constant have similar values. The different IC efficiences of these molecules are therefore determined by the structural differences (amino twist angle) between S1 and S0. A correlation is found between the IC efficiency in these molecules and the twist angle θ. The IC process to S0 starts from the equilibrated S1 state, which is vibronically coupled with S2 due to a small energy gap ΔE(S1,S2). It is therefore concluded that the extent of vibronic coupling and the magnitude of the twist angle θ are the determining factors in the IC process.

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Section: Methodsmentioning

confidence: 99%

“…13 1N5 was made from naphthalene-1-yl-(4-phenoxybutyl)amine and AlCl 3 . 14 This amine resulted from a reaction between 1AN (Merck) and 4-methoxybutylbromide. 15 A synthesis procedure similar to that employed to obtain 1N4 did not lead to the desired product.…”

Section: Methodsmentioning

confidence: 99%

Internal Conversion in 1-Aminonaphthalenes. Influence of Amino Twist Angle

et al. 1999

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“…In methanol, however, some trans addition did occur with an approximate ratio of cis-to-trans addition product of 2:1. The reaction of azetidine with dimethyl fumarate or maleate gave dimethyl (l-azetidinyl)succinate (27) in 57 and 48% yield, respectively. Similarly /3-(1-azetidinyl)propionitrile (28) was formed in 56% yield by the addition of NCHCOOCH3 :nch2ch2cn CH2COOCH3 27 azetidine to acrylonitrile.…”

Section: Miscellaneous N-substituted Azetidinesmentioning

confidence: 99%