Generation of Azines by the Reaction of a Nucleophilic Carbene with Diazoalkanes: A Synthetic and Crystallographic Study

Autor:	Katherine N. Robertson, Hopkins Jm, Bowdridge M, Jason A. C. Clyburne, Hilary A. Jenkins, Cameron Ts
Rok vydání:	2001
Předmět:	chemistry.chemical_compound Crystallography chemistry Nucleophile Charge separation Group (periodic table) Organic Chemistry Carbene Azidotrimethylsilane
Zdroj:	The Journal of Organic Chemistry. 66:5713-5716
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo001515b
Popis:	Reactions of the nucleophilic carbene 1,3-dimesityl-imidazol-2-ylidene (1) with diazofluorene, diphenyldiazomethane, and azidotrimethylsilane were examined. Specifically, carbene 1 reacts with diazofluorene and diphenyldiazomethane to give addition products (azines: 3 and 4, respectively). Compounds 3 and 4 were further characterized in the solid-state by single-crystal X-ray crystallographic studies. [3 (a = 9.7936(6) A, b = 10.0529(7) A, c = 16.251(1) A, alpha = 75.765(1) degrees, beta = 79.711(1) degrees, gamma = 64.321(1) degrees, Z = 2, space group P1); 4 (a = 11.681(3) A, b = 11.861(4) A, c = 21.186(3) A, alpha = 90 degrees, beta = 97.05(2) degrees, gamma = 90 degrees, Z = 4, space group P2(1)/n)]. The structural parameters of 3 and 4 are discussed with reference to previously characterized symmetrical and unsymmetrical azines. Structural data suggest that charge separation is possible in 3.
Databáze:	OpenAIRE
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