Oxidation reactions of a 1-phosphadiene: Synthesis of phosphacyclobutenes

Autor:	Robert H. Neilson, Randall J. Thoma, Bruce A. Boyd
Rok vydání:	1987
Předmět:	Stereochemistry Organic Chemistry chemistry.chemical_element Nuclear magnetic resonance spectroscopy Ring (chemistry) Biochemistry Sulfur Phosphorane Medicinal chemistry Redox Cycloaddition chemistry.chemical_compound chemistry Yield (chemistry) Drug Discovery Methylene
Zdroj:	Tetrahedron Letters. 28:6121-6124
ISSN:	0040-4039
Popis:	Oxidation of the 1-phosphadiene, R2N-PCR-CHCHR (1:R=SiMe3), with Me3SiN3 is accompanied by ring-closure to yield the novel phosphacyclobutene, R2N-P(NR)-CRCH-CHR (2). A structuralisomer of 2 [i.e., R2N-P(NR)-CHCR-CHR(6)] is obtained via the cycloaddition of Me3SiCCH with the (methylene) phosphorane, R2N-P(=NR)=CHR(5). Treatment of 1 with an excess of elemental sulfur affords the disulfide,R2N-P(=S)-S-CR-CHCHR (3), from which removal of one sulfur atom (with Ph3P) results in a rearrangement to another 4-membered ring, R2N-P(=S)-CR=CH-CHR (4).
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e57a1be9f8d263f6aee7a0494c8868bd https://doi.org/10.1016/s0040-4039(00)61824-5 Zobrazit plný text záznamu