Studies on 1:2-dihydro-1-keto-2-thianaphalenes and the synthesis of gladiolic acid

Brown, John Johnston (1954) Studies on 1:2-dihydro-1-keto-2-thianaphalenes and the synthesis of gladiolic acid. PhD thesis, University of Glasgow.

Abstract

1.m-Opianic acid and 4:5-methylenedioxyphthalaldehydic acid have been prepared in good yield from m-meconin and 5:6-methylenedioxyphthalide respectively. 2. A new phthalide, 4:5-methylenedioxyphthalide, has been obtained from piperonylic acid. 3. Reaction of 1:2-dihydro-1-keto-6:7-dimethoxy-2-thianaphthalene-3-carboxylic acid and 1:2-dihydro-1-keto-6:7-methylenedioxy-2-thianaphthalene-3-carboxylic acid with Raney nickel gives 5:6-dimethoxyindam-1-one and 5:6-methylenedioxyindan-l-one respectively. 4. 5:6-Methylenedioxyindan-1-one has been obtained by the action of Raney nickel on hydrastal (6-vinylpiperonal). 5. A mechanism has been suggested for the conversion of 1:2-dihydro-1-keto-2-thianaphtlialenes into indanones using Raney nickel.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Additional Information: Adviser: F S Spring
• Keywords: Organic chemistry
• Date of Award: 1954
• Depositing User: Enlighten Team
• Unique ID: glathesis:1954-73431
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 14 Jun 2019 08:56
• Last Modified: 14 Jun 2019 08:56
• URI: https://theses.gla.ac.uk/id/eprint/73431