A [3.3]Sigmatropic Rearrangement of α,β-Unsaturated Fischer Chromium Carbenes: Synthesis of Alkynol and Dienol Esters

Autor:	Jian Liu, Björn C.G. Söderberg, Shannon N. O'Neil, Angela C. Chisnell
Rok vydání:	2000
Předmět:	Tetramethylammonium Chromate conversion coating Organic Chemistry chemistry.chemical_element Sigmatropic reaction Biochemistry Chloride Medicinal chemistry chemistry.chemical_compound Chromium chemistry Yield (chemistry) Drug Discovery Side product medicine Organic chemistry medicine.drug
Zdroj:	Tetrahedron. 56:5037-5044
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(00)00216-7
Popis:	A novel [3.3]sigmatropic rearrangement of in situ formed α,β-unsaturated Fischer acyloxy carbenes forming alkynol esters is described. For example, reaction of tetramethylammonium pentacarbonyl(1-oxo-2-butenyl)chromate(1-) (4) with 4-methoxybenzoyl chloride gave 2-methyl-3-butyn-2-yl 4-methoxybenzoate (8) in 32% yield. In addition to the rearrangement products, dienol esters formed by a formal β-hydride elimination-reductive elimination sequence were usually isolated. In the above example, 3-methylbuta-1,3-dien-1-yl 4-methoxybenzoate (9) was obtained (16%) as the side product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b015893bb7527e9d39938bb7c6f250f6 https://doi.org/10.1016/s0040-4020(00)00216-7 Zobrazit plný text záznamu Full Text from ScienceDirect