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Development of a Lewis base catalyze...

Collins, William.

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Development of a Lewis base catalyzed selenocyclization reaction.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Development of a Lewis base catalyzed selenocyclization reaction./
Author:	Collins, William.
Description:	345 p.
Notes:	Source: Dissertation Abstracts International, Volume: 71-01, Section: B, page: 0319.
Contained By:	Dissertation Abstracts International71-01B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3391917
ISBN:	9781109571578

Development of a Lewis base catalyzed selenocyclization reaction.
Collins, William.

Development of a Lewis base catalyzed selenocyclization reaction. - 345 p.

Source: Dissertation Abstracts International, Volume: 71-01, Section: B, page: 0319.

Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2009.

The concept of Lewis base activation of selenium Lewis acids has been effectively reduced to practice in the Lewis base catalyzed selenofunctionalization of unactivated olefins. In this reaction, the weakly acidic species, N-phenylselenyl succinimide, is cooperatively activated by the addition of a "soft" Lewis base donor (phosphine sulfides, phosphine selenides, and phosphines), and a weak Bronsted acid activator. Through spectroscopic studies, this form of activation has been shown to lead to the formation of a cationic Lewis base-selenium(II) complex, which is a competent catalyst for the selenolactonization and selenoetherification reaction.

ISBN: 9781109571578Subjects--Topical Terms:

516206
Chemistry, Organic.

Development of a Lewis base catalyzed selenocyclization reaction.
LDR:02381nam 2200277 4500 001 1394087
005 20110419112717.5
008 130515s2009 ||||||||||||||||| ||eng d
020 $a 9781109571578
035 $a (UMI)AAI3391917
035 $a AAI3391917
040 $a UMI $c UMI
100 1 $a Collins, William. $3 1672670
245 1 0 $a Development of a Lewis base catalyzed selenocyclization reaction.
300 $a 345 p.
500 $a Source: Dissertation Abstracts International, Volume: 71-01, Section: B, page: 0319.
500 $a Adviser: Scott E. Denmark.
502 $a Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2009.
520 $a The concept of Lewis base activation of selenium Lewis acids has been effectively reduced to practice in the Lewis base catalyzed selenofunctionalization of unactivated olefins. In this reaction, the weakly acidic species, N-phenylselenyl succinimide, is cooperatively activated by the addition of a "soft" Lewis base donor (phosphine sulfides, phosphine selenides, and phosphines), and a weak Bronsted acid activator. Through spectroscopic studies, this form of activation has been shown to lead to the formation of a cationic Lewis base-selenium(II) complex, which is a competent catalyst for the selenolactonization and selenoetherification reaction.
520 $a A variety of chiral, "soft" Lewis base donors were prepared and tested in the selenofunctionalization reaction. An enantioselective process was never realized. Mechanistic investigations have revealed that the seleniranium ion intermediate (which is formed after delivery of the electrophilic selenium source to the olefin, and is the stereodetermining event in this transformation) is configurationally unstable under the reaction conditions. In particular, rapid deselenylation and subsequent racemization of the seleniranium ion has been shown to occur in the presence of alcohol and olefin nucleophiles. Investigations into retarding the rate of racemization of the seleniranium ion intermediate have revealed that electron-poor and sterically encumbered arylselenides are less prone to racemize in the presence of nucleophiles.
590 $a School code: 0090.
650 4 $a Chemistry, Organic. $3 516206
690 $a 0490
710 2 $a University of Illinois at Urbana-Champaign. $3 626646
773 0 $t Dissertation Abstracts International $g 71-01B.
790 1 0 $a Denmark, Scott E., $e advisor
790 $a 0090
791 $a Ph.D.
792 $a 2009
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3391917