4,5-Dimethylene -1,2-dioxane and derived Diels-Alder adducts

✍ Scribed by Basri Atasoy; Serdar Karaböcek

• Book ID: 104214750
• Publisher: Elsevier Science
• Year: 1992
• Tongue: French
• Weight: 176 KB
• Volume: 33
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)74738-1

✦ Synopsis

This paper reports the syntheses of the previously unknown 4-S-dimethylene-12dioxane (1) and the symmetric bisperoxide 3,4,8,9-tetraoxa-l(6)-bicyclo[4.4.0]decene (2). 2 Compound 1 contains exocyclic diene and 12-dioxane moieties both of which can be madly functionalixed. The diene moiety can react with different dienophiles and form 4,5-substituted cyclohexane (or cyclohexene) annelated-1.2-dioxanes. 3.4~Disubstituted furans can be prepared from the rearrangement of this cycloadduct. Such a sequence is of use in the synthesis of various subtituted multicyclic molecules. 3,4-Disubstituted furans are generally obtained from vinyloxiranes or cxrthiometylene ketoneslp2. These methodologies require the use of anhydrous solvent, strong organic bases and low reaction temperatures. Compound 1 is also of interest for the potential use of furans obtained from rearrangement of the cycloadduct of diene 1 with 1.4-benzoquinone derivatives as precursors of cage molecules which can be formed from intramolecular cycloaddition.