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Sulfur-Participated Cyclization Reaction

Author: XieYongFa
Tutor: ZhouHongWei
School: Zhejiang University
Course: Organic Chemistry
Keywords: Sulfur to participate Indene derivatives Thiophene derivative [3,3] δ rearrangement
CLC: O621.25
Type: Master's thesis
Year: 2010
Downloads: 66
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Abstract


Since the atomic radius of the sulfur atoms than oxygen atoms , a sulfur anion nucleophilicity than the oxygen anion , a sulfur in organic synthesis also easy to form positive ions of the sulfonium compound containing allyl alkenyl sulfide structural unit is also easy occurs [3,3 ] δ is the rearrangement , the sulfur to participate in important means of Construction of the heterocyclic compound in the organic synthesis . In recent years , there are a lot of research workers synthesized by the method of sulfur involved in many of the heterocyclic compounds, the present paper , we also synthesized by the method of using sulfur participation series of indene derivatives and thiophene derivatives . The inden are important structure of many natural products and drug unit, can also be used as precursors in the synthesis of related compounds important synthetic . In the second chapter of the present invention to the alkylthio substituted olefins as raw materials, with trifluoromethanesulfonic anhydride , and an excess of a base (pyridine) synthesized a series of indene derivative exists , the cyclic sulfur in the course of the reaction onium positive ion intermediates mechanism constituting the indene ring , its mechanism has been proved from the side . The new method of synthesis of indene derivatives with no metal catalysis , easy to get raw materials , functional groups applicability good advantages . Thiophene derivative widely used in the synthesis of pharmaceutical , pesticide , dye , functional materials . Chapter III of this paper , we study the sulfur to participate in the five-step tandem reaction : propargyl allenyl rearrangement Claisen rearrangement of sulfur participation the enolization thione , Michael addition and 1,5-H migration to the synthesis of a series of thiophene derivatives , we have studied the optimal reaction conditions for this reaction , the applicability of the functional group reactive deuterated method studied the reaction mechanism of this reaction . We report such synthetic thiophene new reaction requires only under conditions of room temperature , with an organic base of DBU ( 1,5 - two aza two bad [5.4.0] -5 - ene) to fast rate , the higher the yield generate the corresponding product, is the simple method of a synthetic thiophene derivative .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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