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

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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:

http://fulir.irb.hr/id/eprint/4014

DOI:

10.3762/bjoc.7.36