Thiele's acid revisited: Isolation and characterization of two minor products formed by carbonation of cyclopentadienide anion

Autor:	Irishi N. N. Namboothiri, S. B. Lewis, William H. Watson, Mariusz Krawiec, Alan P. Marchand
Rok vydání:	1998
Předmět:	Sodium cyclopentadienide chemistry.chemical_compound Chemistry Stereochemistry Intramolecular force Carbonation Organic Chemistry Drug Discovery Biochemistry Medicinal chemistry Ion
Zdroj:	Tetrahedron. 54:12691-12698
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(98)00770-4
Popis:	Carbonation of sodium cyclopentadienide leads to the formation of 3aα,4α,7α,7aα-tetrahydro-4,7-methano-1H-indene-2,6-dicarboxylic acid [i.e., “Thiele's acid”, 2i (R = H), 60%] along with several isomeric C12H12O4 minor products. The dimethyl esters of two of these minor products, i.e., dimethyl 3aα,4α,7α,7aα-tetrahydro-4,7-methano-1H-indene-2,4-dicarboxylate [2a (R = Me), 13%) and the corresponding 3a,6-dicarboxylate [2n (R = Me), 1%] have been isolated and characterized. Intramolecular [2 + 2] photocyclization of 2a (R = Me) afforded 3a (R = Me) (30%), whose structure was established unequivocally by application of X-ray crystallographic techniques.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::e2bde8fb25887e94a90b403477992c38 https://doi.org/10.1016/s0040-4020(98)00770-4 Zobrazit plný text záznamu Full Text from ScienceDirect