Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide

Cindro, Nikola; Horvat, Margareta; Mlinarić-Majerski, Kata; Griesbeck, Axel G.; Basarić, Nikola (2011) Photoinduced homolytic C–H activation in N-(4-homoadamantyl)phthalimide. Beilstein journal of organic chemistry, 7 . pp. 270-277. ISSN 1860-5397

Preview

PDF - Published Version - article Available under License Creative Commons Attribution. Download (414kB) | Preview

Abstract

N-(4-homoadamantyl)phthalimide (5) on excitation and population of the triplet excited state underwent intramolecular H-abstractions and gave products 6 and 7. The major product, exo-alcohol 6 was a result of the regioselective δ H-abstraction and the stereoselective cyclization of the 1, 5-biradical. Minor products 7 were formed by photoinduced γ H-abstractions, followed by ring closure to azetidinols and ring enlargement to azepinediones. The observed selectivity to exo-alcohol 6 was explained by the conformation of 5 and the best orientation and the availability of the δ-H for the abstraction.

Item Type:	Article
Uncontrolled Keywords:	homoadamantanes ; photoinduced H-abstraction ; phthalimides
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Organic Chemistry and Biochemistry
Projects:	Project title Project leader Project code Project type Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima- Kata Majerski 098-0982933-2911 MZOS Fotokemija policikličkih molekula: od istraživanja mehanizma reakcije do novih lijekova i medicinskih primjena- Nikola Basarić UIP-02.05/25 HRZZ
Depositing User:	Nikola Basarić
Date Deposited:	17 Apr 2018 16:25
URI:	https://fulir.irb.hr:/id/eprint/4014
DOI:	10.3762/bjoc.7.36

Actions (login required)

View Item