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In search of a more reactive and con...

Vodnala, Thirupathi.

In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent.

Record Type:	Electronic resources : Monograph/item
Title/Author:	In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent.
Author:	Vodnala, Thirupathi.
Description:	67 p.
Notes:	Source: Masters Abstracts International, Volume: 54-03.
Notes:	Adviser: VINOD THOTTUMKARA.
Contained By:	Masters Abstracts International54-03(E).
Subject:	Organic chemistry.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=1584742
ISBN:	9781321597226

In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent.
Vodnala, Thirupathi.

In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent. - 67 p.

Source: Masters Abstracts International, Volume: 54-03.

Thesis (M.S.)--Western Illinois University, 2015.

Functional groups in organic molecules play a pivotal role and their oxidation is of paramount importance in synthetic organic chemistry. In recent years, the use of hypervalent iodine reagents as mild oxidants has gained prominence due to the selectivity exhibited during oxidation and their benign nature. Two main classes of polyvalent or hypervalent iodine species, lambda 3 and lambda5-iodanes are widely employed in catalytic oxidation reactions. The parent lambda3 compound (diacetoxyiodo) benzene, PhI(OAc)2 or DAIB, 1 is well known as an oxidizing agent. (Diacetoxyiodo)benzene is primarily employed in functionalization of alkenes, conversion of primary alcohols to selective aldehydes, carbon-carbon cleavage and oxidative decarboxylation. (Diacetoxyiodo)benzene was first synthesized by using iodosylbenzene by dissolving it in hot acetic acid. (Diacetoxyiodo)benzene is now routinely prepared by oxidizing iodoarenes in glacial acetic acid either by peracetic acid, sodium perborohydrate or chromium oxide. Various derivatives of DAIB have been reported. Chemists continue to search for a more reactive derivative of DAIB that exhibits greater oxidative properties with more benign nature.

ISBN: 9781321597226Subjects--Topical Terms:

708640
Organic chemistry.

In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent.
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020 $a 9781321597226
035 $a (MiAaPQ)AAI1584742
035 $a AAI1584742
040 $a MiAaPQ $c MiAaPQ
100 1 $a Vodnala, Thirupathi. $3 730215
245 1 0 $a In search of a more reactive and convenient eco-friendly hypervalent iodine oxidizing agent.
300 $a 67 p.
500 $a Source: Masters Abstracts International, Volume: 54-03.
500 $a Adviser: VINOD THOTTUMKARA.
502 $a Thesis (M.S.)--Western Illinois University, 2015.
520 $a Functional groups in organic molecules play a pivotal role and their oxidation is of paramount importance in synthetic organic chemistry. In recent years, the use of hypervalent iodine reagents as mild oxidants has gained prominence due to the selectivity exhibited during oxidation and their benign nature. Two main classes of polyvalent or hypervalent iodine species, lambda 3 and lambda5-iodanes are widely employed in catalytic oxidation reactions. The parent lambda3 compound (diacetoxyiodo) benzene, PhI(OAc)2 or DAIB, 1 is well known as an oxidizing agent. (Diacetoxyiodo)benzene is primarily employed in functionalization of alkenes, conversion of primary alcohols to selective aldehydes, carbon-carbon cleavage and oxidative decarboxylation. (Diacetoxyiodo)benzene was first synthesized by using iodosylbenzene by dissolving it in hot acetic acid. (Diacetoxyiodo)benzene is now routinely prepared by oxidizing iodoarenes in glacial acetic acid either by peracetic acid, sodium perborohydrate or chromium oxide. Various derivatives of DAIB have been reported. Chemists continue to search for a more reactive derivative of DAIB that exhibits greater oxidative properties with more benign nature.
520 $a The current project primarily focuses on synthesizing SF5-substituted DAIB and subsequently investigating its oxidative properties. We hypothesized that substitution of strong electron withdrawing group (-SF5) on the arene ring will enhance its potential as an oxidizing agent. Commercially available p-tolylsulfur pentafluoride, 61 was chosen as a convenient starting material for the synthesis of 60. The first step of the synthesis involved the nitration of 61 to give 62. Reduction of 62 to yield 63 followed by diazotization and iodination gave 64. Our initial attempts to oxidize the iodine atom of 64 to its hypervalent state (III) was failed. We finally achieved the synthesis of 60 by using sodium perborate (NaBO3.4H2O), as oxidant on 64. All new derivatives were obtained in good yields and fully characterized by 1H NMR, 13C NMR, IR and 19F NMR spectroscopic techniques. Use of 60 in successful co-iodination of electron deficient alkenes is also reported.
590 $a School code: 6012.
650 4 $a Organic chemistry. $3 708640
690 $a 0490
710 2 $a Western Illinois University. $b Chemistry. $3 660204
773 0 $t Masters Abstracts International $g 54-03(E).
790 $a 6012
791 $a M.S.
792 $a 2015
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=1584742