ORBITAL SYMMETRY CONTROL IN THE NITRONE-OXAZIRIDINE SYSTEM.NITRONE PHOTOSTATIONARY STATES

PDF Version Also Available for Download.

Description

Recent the orbital symmetry rules have been shown to apply to hetero-atom systems such as nitrone thermal cycloaddition reactions and the thermal and photochemical aziridine ring cleavage at the C-C bond. The concerted photocyclization is disrotatory and the reverse thermal cleavage is conrotatory in these molecules with four {pi} electrons. In contrast to the azomethine ylide-aziridine system, the stereochemistry of the nitrone photocyclization to oxaziridine can only be observed on carbon and nitrogen atoms because the oxygen atom has lone pair electrons instead of substituents. For the reverse thermal ring opening of oxaziridine to the nitrone, the two possible conrotatory ... continued below

Physical Description

6 p.

Creation Information

Splitter, Janet S.; Su, Tah-mun; Ono, Howard & Calvin, Melvin. June 1, 1971.

Context

This article is part of the collection entitled: Office of Scientific & Technical Information Technical Reports and was provided by UNT Libraries Government Documents Department to Digital Library, a digital repository hosted by the UNT Libraries. More information about this article can be viewed below.

Who

People and organizations associated with either the creation of this article or its content.

Publisher

Provided By

UNT Libraries Government Documents Department

Serving as both a federal and a state depository library, the UNT Libraries Government Documents Department maintains millions of items in a variety of formats. The department is a member of the FDLP Content Partnerships Program and an Affiliated Archive of the National Archives.

Contact Us

What

Descriptive information to help identify this article. Follow the links below to find similar items on the Digital Library.

Description

Recent the orbital symmetry rules have been shown to apply to hetero-atom systems such as nitrone thermal cycloaddition reactions and the thermal and photochemical aziridine ring cleavage at the C-C bond. The concerted photocyclization is disrotatory and the reverse thermal cleavage is conrotatory in these molecules with four {pi} electrons. In contrast to the azomethine ylide-aziridine system, the stereochemistry of the nitrone photocyclization to oxaziridine can only be observed on carbon and nitrogen atoms because the oxygen atom has lone pair electrons instead of substituents. For the reverse thermal ring opening of oxaziridine to the nitrone, the two possible conrotatory motions of C-O bond cleavage should result in a mixture of the cis and trans-isomers of the nitrone, in contrast to the photoclosure which should be stereospecific.

Physical Description

6 p.

Source

  • Journal Name: Journal of American Chemical Society; Journal Volume: 0; Journal Issue: 0; Related Information: Journal Publication Date: 0

Language

Item Type

Identifier

Unique identifying numbers for this article in the Digital Library or other systems.

  • Report No.: UCRL--20858
  • Grant Number: DE-AC02-05CH11231
  • Office of Scientific & Technical Information Report Number: 928345
  • Archival Resource Key: ark:/67531/metadc893302

Collections

This article is part of the following collection of related materials.

Office of Scientific & Technical Information Technical Reports

What responsibilities do I have when using this article?

When

Dates and time periods associated with this article.

Creation Date

  • June 1, 1971

Added to The UNT Digital Library

  • Sept. 27, 2016, 1:39 a.m.

Description Last Updated

  • Nov. 3, 2016, 8:17 p.m.

Usage Statistics

When was this article last used?

Yesterday: 0
Past 30 days: 1
Total Uses: 2

Interact With This Article

Here are some suggestions for what to do next.

Start Reading

PDF Version Also Available for Download.

Citations, Rights, Re-Use

Splitter, Janet S.; Su, Tah-mun; Ono, Howard & Calvin, Melvin. ORBITAL SYMMETRY CONTROL IN THE NITRONE-OXAZIRIDINE SYSTEM.NITRONE PHOTOSTATIONARY STATES, article, June 1, 1971; Berkeley, California. (digital.library.unt.edu/ark:/67531/metadc893302/: accessed September 25, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.