Absolute configuration of spirobiphthalide

✍ Scribed by Sanji Hagishita; Kaoru Kuriyama

• Book ID: 104243214
• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 192 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)92094-5

✦ Synopsis

Assignments of absolute configuration to chiral C2 spirans have been established ;Ir chemical and crystallographic methods' and theoretical calculations of CD spectra .2 Chircptical properties of spirans with fused aromatic rings are of interest to us and we have already reported the properties and the assignment of the absolute configuration of a series of 3,3,3',3'-tetramethyl-1 ,I'-spirobiindans .2r3 3,3'-Spirobiphthalide-6,6'-dicarboxylic acid (3 has already been resolved into two enantiomem by W. H. Mills and C. R. Nodder.4 This heterocyclic C, spiran is conformationally rigid and it is interesting to predict the absolute configuration and to see the Spiro conjugation5 in comparison with the other spirans in which Spiro conjugation has been damonstrated.6 (+)-l[ hrn (As): 290 (+1.42), 281 (+1.42), 270 (+2.04), 242 (+2J.7), 218 (-121. ), 207 (+75. ).