Selective syntheses of substituted 6-alkyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalenes

✍ Scribed by John J. Parlow

• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 866 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)86337-7

✦ Synopsis

in 80-95% yreld. Selective derivadzadon at rhe 5-andlor 7-positrons of 6-alkyl-1 ,I-dbnerhyl-I ,2,3.4-lerrahydronlenes was aclueved by As part of a systematic search for herbicidal compounds, a series of substituted 6-alkyl-l,l-dimethyl-1,2,3,4-tetrahydronaphthalenes were prepared. This project started when compound (1)1 demonstrated significant preemergent activity on economically important narrowleaf weeds. Compound (1) was prepared by Tanis et al.2 using a Diels-Alder reaction with methyl propiolate and 6,6-dimethyl-1-vinylcyclohexene to afford the hexahydronaphthalene followed by aromatization using DDQ to yield compound (1). In our synthetic follow up, we chose the method used by Bogert3 et al. to prepare the teaahydronaphthalene intermediate (3). This paper describes the synthesis of compounds (3) and the regioselectivity of electrophilic substitution at the 5 and 'I-positions of the tetralin ring.