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Photochemistry of beta-cyclopropylme...

Michigan State University.

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Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone./
Author:	Govardhan, Varsha Subodh.
Description:	48 p.
Notes:	Adviser: Peter J. Wagner.
Contained By:	Masters Abstracts International40-02.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=1405940
ISBN:	9780493341934

Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone.
Govardhan, Varsha Subodh.

Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone. - 48 p.

Adviser: Peter J. Wagner.

Thesis (M.S.)--Michigan State University, 2001.

Intramolecular hydrogen abstraction is one of the major outcomes of irradiating carbonyl compounds which have a molecular structure that allows a close approach between the excited carbonyl compound and a sp3 carbon within the same molecule. This process is favored from the gamma carbon due to geometric and thermodynamic considerations. However abstraction from the delta carbon is a competing reaction that can occur with highly activated delta C--H bonds or in the absence of gamma hydrogens.

ISBN: 9780493341934Subjects--Topical Terms:

516206
Chemistry, Organic.

Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone.
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008 100629s2001 ||||||||||||||||| ||eng d
020 $a 9780493341934
035 $a (UMI)AAI1405940
035 $a AAI1405940
040 $a UMI $c UMI
100 1 $a Govardhan, Varsha Subodh. $3 1017805
245 1 0 $a Photochemistry of beta-cyclopropylmethoxy propiophenone and o-benzyl benzophenone.
300 $a 48 p.
500 $a Adviser: Peter J. Wagner.
500 $a Source: Masters Abstracts International, Volume: 40-02, page: 0451.
502 $a Thesis (M.S.)--Michigan State University, 2001.
520 $a Intramolecular hydrogen abstraction is one of the major outcomes of irradiating carbonyl compounds which have a molecular structure that allows a close approach between the excited carbonyl compound and a sp3 carbon within the same molecule. This process is favored from the gamma carbon due to geometric and thermodynamic considerations. However abstraction from the delta carbon is a competing reaction that can occur with highly activated delta C--H bonds or in the absence of gamma hydrogens.
520 $a beta-Cyclopropylmethoxy propiophenone proved to be an interesting example of the latter. In this case 1,5 biradical formation was followed by subsequent radical ring opening of the cyclopropyl moiety as opposed to cyclopentanol formation seen with other compounds such as beta-ethoxypropiophenone.
520 $a Photoenolization followed by electrocyclic ring closure to stereoselectively form the cyclobutenol was the result of irradiating o-benzyl benzophenone, which was a classic example of photoenolization. To reinforce our understanding of the ketone → enol → benzocyclobutenols chronology, this process was also studied in the solid state. The difference in the diastereoselectivity of cyclobutenol formation between the solid and liquid state confirms the fact that it is governed by the geometry of the biradical initially formed by hydrogen abstraction.
590 $a School code: 0128.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Radiation. $3 1017804
690 $a 0490
690 $a 0754
710 2 $a Michigan State University. $3 676168
773 0 $t Masters Abstracts International $g 40-02.
790 $a 0128
790 1 0 $a Wagner, Peter J., $e advisor
791 $a M.S.
792 $a 2001
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=1405940