Introduction of benzyl triphenyl phosphonium tribromide(BTPTB) as a new and efficient oxidizing agent

mousazadeh, Seyyed Alireza and Imanzadeh, Gholam Hassan and Shirini, Farhad and zamanloo, Mohammadreza (2009) Introduction of benzyl triphenyl phosphonium tribromide(BTPTB) as a new and efficient oxidizing agent. Masters thesis, University of Mohaghegh Ardabili.

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Abstract

In this study oxidation of alcohols and oxidative deprotection of trimethyl silyl, tetrahydropyranyl and methoxy methylethers to their corresponding carbonyl compounds is investigated by using BTPTB. In addition, tetrahydropyralation and methoxymethylation of different types of alcohols with DHP and MOM were carried out in the presence of BTPTB in good to high yields. Trimethyl silylation of a variety of alcohols has also been performed by using HMDS in the presence of BTPTB under reflux conditions. Trimethylsilyl ethers were also deprotected to parent alcohols in the presence of BTPTB at room temperature. Benzylic and primary, secondary and tertiary aliphatic alcohols were efficiently converted to thir corresponding esters with acetic anhydride in the presence of BTPTB. BTPTB was also used as an efficient reagent for the oxidation of sulfides to their corresponding sulfoxides in refluxing mixture of CH3CN and H2O. Oximes and semicarbazones were converted to their corresponding carbonyl compounds by using BtPTB in refluxing mixture of MeOH and H2O.

Item Type: Thesis (Masters)
Persian Title: معرفي بنزيل تري فنيل فسفونيوم تري برميد بعنوان يك عامل اكسيد كننده جدید و مؤثر
Persian Abstract: در اين مطالعه اکسايش الکلها و محافظت زدايي اکسايشي تري متيل سايليل ، تترا هيدرو پيرانيل و متوکسي متيل اترها با استفاده از BTPTB به ترکيبات کربونيل متناظر مورد بررسي قرار گرفت . به علاوه تترا هيدرو پيرانيله کردن و متوکسي متيله کردن انواع مختلف الکل ها با DHP و MOM در حضور BTPTB با بازده خوبي انجام شد . همچنين تري متيل سايليله کردن انواعي از الکل ها با استفاده از HMDS در حضور BTPTB تحت شرايط رفلاکس انجام گرفت . تري متيل سايليل اترها در حضور اين واکنشگر و در دماي اتاق به الکل هاي اوليه تبديل مي شوند . الکل هاي آليفاتيکي و بنزيلي نوع اول ، دوم ، و سوم به طور موثري توسط استيک انيدريد و در حضور BTPTB به استرهاي متناظر تبديل شدند . از BTPTB همچنين مي توان به عنوان يک واکنشگر موثر براي اکسايش سولفيد ها به سولفوکسيد هاي متناظر در مخلوط آب و استونيتريل تحت شرايط رفلاکس استفاده کرد . BTPTB همچنين قادر است تبديل اکسيمها و سمي کاربازونها به ترکيبات کربونيل دار متناظر را به خوبي و با بهره هاي بالا تسريع نمايد. اين دسته از واکنشها در مخلوط آب و متانول تحت شرايط رفلاکس انجام پذير هستند.
Supervisor:
SupervisorE-mail
Imanzadeh, Gholam HassanUNSPECIFIED
Shirini, FarhadUNSPECIFIED
Advisor:
AdvisorE-mail
zamanloo, MohammadrezaUNSPECIFIED
Subjects: Faculty of Basic Sciences > Department of Chemistry
Divisions > Faculty of Basic Sciences > Department of Chemistry
Divisions: Subjects > Faculty of Basic Sciences > Department of Chemistry
Faculty of Basic Sciences > Department of Chemistry
Date Deposited: 09 Jul 2019 07:21
Last Modified: 09 Jul 2019 07:21
URI: http://repository.uma.ac.ir/id/eprint/7299

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