Propellanes. L. Further support for control by secondary orbital overlap during Diels-Alder reactions of certain propellanes,

✍ Scribed by M. Kaftory; M. Peled; D. Ginsburg

• Publisher: John Wiley and Sons
• Year: 1979
• Tongue: German
• Weight: 199 KB
• Volume: 62
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19790620446

✦ Synopsis

Abstract

In contrast to the behavior of 4‐substituted‐1,2, 4‐triazoline‐3, 5‐diones which add to the syn‐face of the cyclohexadiene with respect to the hetero‐ring in propellanes of type 1, dienophiles containing a C, C double bond instead of an N, N double bond add exclusively to the anti‐face of the same substrates. This supports our thesis that these reactions are controlled by secondary orbital interaction between the N, N dienophiles and the hetero‐ring of the substrates, an interaction which cannot exist in the C, C dienophiles.