A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

✍ Scribed by Joseph Almog; Yirmi Zehavy; Shmuel Cohen

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 171 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00622-1

✦ Synopsis

1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.