The relative reactivity of cyclic ketones towards methyltitanium reagents

Reetz, M. T.; Hugel, H.; Dresley, K.

doi:10.1016/S0040-4020(01)89936-1

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The relative reactivity of cyclic ketones towards methyltitanium reagents

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引用

Reetz, M. T., Hugel, H., & Dresley, K. (1987). The relative reactivity of cyclic ketones towards methyltitanium reagents. Tetrahedron, 43(1), 109-114. doi:10.1016/S0040-4020(01)89936-1.

引用: https://hdl.handle.net/21.11116/0000-000E-7D54-8

要旨

The relative rates of the addition of CH₃TiCl₃ and CH₃Ti (OCHMe₂)₃ to various cyclic ketones of different ring size have been determined. In contrast to CH₃Li and CH₃MgCl, significant rate differences were observed. For CH₃TiCl₃ (at 18°C) the following decreasing order in rate pertains, the numbers symbolizing the ring size: 6 > 5 > 7 > 15 > 8 > 12 > 9 > 11 > 10. For CH₃Ti (OCHMe₂)₃ (at +22°C) it is slightly different: 6 > 5 > 7 > 8 > 15 > 9 > 12 > 13 > 11 > 10. Most of the results can be explained on the basis of Brown's hypothesis of I-strain. However, the 15-membered ring cyclopentadecanone represents the major “irregularity”.