3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-dioxide: unusual C—O—C ether bond lengths and reactivity

Barkley, J. V.; Cristiano, Maria Lurdes Santos; Johnstone, Robert A. W.; Loureiro, Rui M. S.

http://hdl.handle.net/10400.1/4237

Use this identifier to reference this record.

Name:	Description:	Size:	Format:
3- (E)-But-2-enoxy- 1,2-benzisothiazole.pdf		437.93 KB	Adobe PDF	Download

Send Feedback

Authors

Barkley, J. V.

Cristiano, Maria Lurdes Santos

Johnstone, Robert A. W.

Loureiro, Rui M. S.

Abstract(s)

Ethers such as the title compound, C~HIINO3S, (1), rearrange thermally to give N-allyl isomers, (2), in high yield. The X-ray structure determination of the title ether shows a central C--O--C linkage which has one very short (notional) C--O single bond and one exceptionally long single C--O bond. The thermal migration of allyl from the O to the N atom involves the breaking of one of the ether bonds in (1) and a shortening of the other as it becomes a formal carbonyl group in the product (2). The rearrangement is thus considerably assisted by the ground-state structure of the starting ether, in which the bond to be broken is already stretched and the one that is to form a carbonyl group is already a substantial partial double bond.

URI

http://hdl.handle.net/10400.1/4237

Citation

Barkley, J. V.; Cristiano, M. L. S.; Johnstone, R. A. W.; Loureiro, R. M. S. 3-( E )-But-2-enoxy-1,2-benzisothiazole 1,1-Dioxide: Unusual C—O—C Ether Bond Lengths and Reactivity, Acta Crystallographica Section C Crystal Structure Communications, 53, 3, 383-386, 1997.