Application of trichloroisocyanuric acid and triphenylphosphine in the efficient one-pot conversion of benzylic silyl and tetrahydropyranyl ethers to gem-dichlorides

سال انتشار: 1398
نوع سند: مقاله کنفرانسی
زبان: انگلیسی
مشاهده: 190

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شناسه ملی سند علمی:

ISOC27_297

تاریخ نمایه سازی: 19 اسفند 1399

چکیده مقاله:

Geminal dihalides form an important group of organic compounds due to their applications in various fields such as pharmaceutical and agricultural industries or in organic synthesis such as synthesis of some biological active heterocyclic compounds1 and polymers2. A known route for the synthesis of these valuable compounds is based on using aldehyde and ketone sources. Various methods have been reported in this area.3 However, some these methods suffer from some disadvantages such as use of an unusual reagent with low accessibility, formation of undesired products, long reaction times, use of acidic conditions and low yields. On the other hand, the methods converting alcohols to gem-dihalides are very scarce4 and as far as we know, there is not report on the one-pot and oxidative conversion of trimethylsilyl (TMS) or tetrahydropyranyl (THP) ethers to gem-dihalides in the literature. Now with the above descriptions and in continuation of our previous works on the synthesis of gem-dihalides,4, 5 we describe for the first time an efficient one-pot oxidative conversion of benzylic both silyl and tetrahydropyranyl ethers to gem-dichlorides using trichloroisocyanuric acid (TCCA) and triphenylphosphine (PPh3) in good to excellent yields under neutral conditions (Scheme 1). This method is tolerated by a variety of other functional groups.

نویسندگان

Roqayeh Khadem,

School of Chemistry, Damghan University, Damghan, ۳۶۷۱۵-۳۶۴, Iran

Ghasem Aghapour

School of Chemistry, Damghan University, Damghan, ۳۶۷۱۵-۳۶۴, Iran