STEREOSPECIFIC FORMATION OF A 1,2λ3 -AZAPHOSPETANE IN THE THERMOLYSIS OF BIS[BIS(DIISOPROPYLAMINO)PHOSPHANYL] DIAZOMETHANE

Autor:	M. Dartiguenave, Marie-Joelle Menu, Antoine Baceiredo, Y. Dartiguenave, Guy Bertrand
Rok vydání:	1990
Předmět:	Stereochemistry Diazomethane Organic Chemistry Substituent Diastereomer Crystal structure Ring (chemistry) Biochemistry Medicinal chemistry Inorganic Chemistry chemistry.chemical_compound Stereospecificity chemistry Carbene Isopropyl
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 47:327-334
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426509008037986
Popis:	Heating of bis[bis(diisopropylamino)phosphanyl]diazomethane 7. in refluxing benzene for 48 hours, quantitatively led to the corresponding 1.2λ3-azaphosphetane 9 as only one diastereoisomer. This result is explained in terms of carbene insertion into a methin-CH bond of an isopropyl substituent. The regiospecificity and the stereospecificity of the ring closure is discussed. Treatment of 9 with elemental sulfur afforded the corresponding 1.2.2λ3-azathiophosphetane 10 which has been characterized b X ray crystallo raphy: C25H56N4P2S2, space group P2(l)/n, a = 13.628 (3) A, 6 = 19.369 (5) A, c 112.485 (4) A, V = 3073 (3) A3.
Databáze:	OpenAIRE
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