## Abstract Photoexcited 3‐acetylbenzo[__b__]thiophene (1c) adds 2‐morpholinopropenenitrile (2a) in a [2 + 2] mode at the C2C3 bond regioselectively but stereounselectively with formation of cyclobuta[__b__][1]benzothiophenes 3a and 4a. In addition, the isomeric adduct 5 is formed from 2a and ex
NMR analyses of two isomeric cyclobutanes from a [2 + 2] photocycloaddition
✍ Scribed by David E. Minter; Christopher D. Winslow; William H. Watson; Satish Bodige
- Publisher
- John Wiley and Sons
- Year
- 2002
- Tongue
- English
- Weight
- 92 KB
- Volume
- 40
- Category
- Article
- ISSN
- 0749-1581
- DOI
- 10.1002/mrc.1035
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✦ Synopsis
Abstract
Complete ^1^H and ^13^C NMR assignments are reported for two isomeric cyclobutanes generated from the photochemical [2 + 2] cycloaddition of N‐methylisocarbostyril and 4‐methoxy‐3‐buten‐2‐one. The reaction is 100% regioselective and demonstrates the potential synthetic utility of de Mayo type reactions using an isocarbostyril and a stable β‐dicarbonyl enol derivative. Copyright © 2002 John Wiley & Sons, Ltd.
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## Abstract MNDO and STO‐3G calculations rationalize the relative instability of the title propellanes vis‐à‐vis the title products that are formed exclusively.