Abstract
MoCl5 is applied as efficient agent in allylic chlorination of terpenic olefins in the presence of NaOCl as chlorine donor. Various terpenes are converted to the corresponding allylic chlorides in moderate to good yield under mild and optimized reaction conditions. Different molybdenum precursors are also studied. Among them, MoO3 gives good yield, but after a longer reaction time.
Highlights
We have reported that allylic amines, alcohols, ketones and alkoxycarbonyl derivatives can be obtained in good yields by the metal complex catalyzed amination, oxidation and alkoxycarbonylation of some monoterpenes.[5,6,7]
In line with our continuous interest in the functionalization of natural terpenic olefins,[5,6,7] we report here the result of our investigation on the allylic chlorination using a combination of sodium hypochlorite and molybdenum pentachloride
Allylic chlorination of b-pinene promoted by molybdenumchloride
Summary
Allylic chlorinated terpenes represent a sustainable supply of intermediates for several segments of the fine chemical industry, e.g., the manufacture of flavors and fragrances.[1,2,3,4] Previously, we have reported that allylic amines, alcohols, ketones and alkoxycarbonyl derivatives can be obtained in good yields by the metal complex catalyzed amination, oxidation and alkoxycarbonylation of some monoterpenes.[5,6,7] Chlorination represents a valuable pathway to produce versatile starting materials that are widely used in synthetic organic chemistry.[8,9,10,11] Chloride compounds can be prepared directly by bubbling molecular chlorine, but the difficulty of handling chlorine gas limits this procedure.[12]. The reaction was conducted firstly using various concentrations of MoCl5 in the presence of NaOCl at room temperature in different reaction times (Table 1). In the presence of NaOCl, no corresponding chlorinated product was observed even after stirring for a long reaction time (entry 1). The same result is observed when using MoCl5 without NaOCl (entry 2) even at high temperature (80 °C).
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