75311-77-2Relevant academic research and scientific papers
Short and versatile two-carbon ring expansion reactions by thermo-isomerization: Novel straightforward synthesis of (±)-muscone, nor- and homomuscones, and further macrocyclic ketones
Nagel, Matthias,Hansen, Hans-Jürgen,Fráter, Georg
, p. 280 - 284 (2007/10/03)
Thermo-isomerization of 1-vinyl substituted medium-and large-ring cycloalkanol derivatives in a flow reactor system at temperatures of 600°C to about 650°C leads directly to the ring-expanded macrocyclic ketones. Alkyl substituents at the vinylic moiety are transferred locospecifically to the ring-expanded ketone as corresponding α-, and β-substituents, respectively. This novel thermal 1,3-C shift reaction therefore provides a new access to short syntheses of many alkyl-substituted macrocyclic ketone derivatives [e.g. (±)-muscone and analogues] in a systematic manner.
