17697-67-5

Upstream product

• 926-62-5 isobutylmagnesium bromide 
• 104-55-2 3-phenyl-propenal 
• 1025913-06-7 (E)-4-Benzotriazol-1-yl-2-methyl-6-phenyl-hex-5-en-3-ol 
• 873653-98-6 3,4-epithio-5-methyl-1-phenyl-(E)-1-hexene 
• 66730-62-9 C₅H₈O₂^(2-)*2Li⁽¹⁺⁾ 
• 171193-30-9 1-(γ-phenylallyl)benzotriazole 
• 227466-03-7 (E)-4-<(5,5-Dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)sulfanyl>-5-methyl-1-phenylhex-1-en-3-one 
• 226921-17-1 O,O-Diethyl S-(1-isopropyl-4-phenyl-2oxobut-3-enyl)thiophosphate 
• 2892-18-4 (E)-5-methyl-1-phenylhex-1-en-3-one 
• 873654-04-7 thiophosphoric acid O,O'-diisopropyl ester S-(1-isopropyl-2-oxo-4-phenyl-but-3-enyl) ester 
• 80674-44-8 threo-3-Hydroxy-2-isopropyl-5-phenyl-(E)-4-pentensaeure 

Downstream Products

• 119420-97-2 4-acetoxy-5-methyl-1-phenylhex-1-en-3-ol 
• 119420-98-3 3-acetoxy-5-methyl-1-phenylhex-1-en-4-ol 
• 119421-03-3 3,4-diacetoxy-5-methyl-1-phenylhex-1-ene 
• 65248-49-9 C₁₃H₁₆O 
• 361447-74-7 C₁₃H₁₆O 
• 81757-61-1 4-isopropyl-7-phenyl-4,7-dihydroisobenzofuran-1,3(7aH,3aH)-dione 

Relevant academic research and scientific papers

A general one-pot synthesis of vinyl-thiiranes and conjugated dienes

The first general synthesis of vinyl-thiiranes 7 and an effiecient preparation of conjugated dienes 8 and 9 is presented. Methodology described for the preparation of these compounds is based on the corresponding readily available thiophosphates 1 and selenophosphates 2.

A general one-pot synthesis of vinyl-thiiranes and conjugated dienes

The first general synthesis of vinyl-thiiranes 5 and an efficient preparation of conjugated dienes 6 and 7 based on thio, and selenophosphates is described.

Trans-Selective Olefination of Carbonyl Compounds by Low-Valent Titanium-Mediated Dehydroxybenzotriazolylation

Lithiation with n-butyllithium of a variety of benzotriazole derivatives 1a-f and 5a-d, all containing a proton α to the benzotriazolyl moiety, gave anions which underwent addition to aliphatic, aromatic, and α,β-unsaturated aldehydes and cyclic and acyclic ketones. The resultant N-(β-hydroxyalkyl)benzotriazole derivatives 3a-m, 6a-g, 9a-d, and 10a were dehydroxybenzotriazolylated when treated with low-valent titanium to give alkenes 4a-m, dienes 7a- j, and triene 11a, with selectivity for the trans isomers without separation of diastereoisomeric intermediates. This method offers an alternative to the three most frequently used methods for the formation of alkenes from carbonyl compounds-the Wittig, Peterson, and Julia reactions-especially in the formation of tri- and tetrasubstituted alkenes.

Additions of Carboxylic Acid Dianions to α,β-Unsaturated Carbonyl Compounds - Control of the 1,2-/1,4-Regioselectivity by Steric Substituent Effects

Dilithium carboxylic acid dianions 1 attack α,β-unsaturated aldehydes (2) 1,2-regiospecifically with formation of the unsaturated β-hydroxy carboxylic acids 3/4.Additionally, the addition of the phenylacetate dianion 1a can be conducted to the threo-isomer with high selectivity by reversible reaction. - α,β-Enones (8) add 1 irreversibly in 1,2- and 1,4-position.Depending on the substitution pattern, the whole range from pure 1,2- to pure 1,4-adduct is covered.The influence of the 1-counterion M and of the solvent is significant; the 1,4-portion increases with the complexing effect of M and with the Lewis-basicity of the solvent.