33557-42-5

Upstream product

• 89-82-7 pulegone 
• 107-05-1 3-chloroprop-1-ene 
• 89-82-7 pulegone 
• 106-95-6 allyl bromide 
• 2622-05-1 allylmagnesium bromide 

Downstream Products

• 113388-13-9 (3R)-3,7,7,8-tetramethylbicyclo<4.3.0>nona-1(6),8-diene 
• 108762-96-5 (5R)-5-methyl-1-(2-propen-1-yl)-2-(2-propen-2-yl)cyclohexene 
• 70855-67-3 (7R)-4,4,7-trimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 

Relevant academic research and scientific papers

Unusual reactivity of bicyclo[2.2.1]heptene derivatives during the ozonolysis

This paper describes mechanistic studies on the ozonolysis of bicyclo[2.2.1]heptene derivatives 6 and 7 obtained from (R)-(+)-pulegone through the cyclopentadiene 5 and its Diels-Alder reaction with maleic anhydride. The ozonolysis of the tricyclic diol 7

Palladium-mediated cyclization of 1,5-hexadien-3-ols to 1-methyl-1,3-cyclopentadienes

Treatment of 1,5-hexadien-3-ols in acetic acid by Pd(o) [Pd(PPh3)4] led to 1-methyl-1,3-cyclopentadienes. Cyclization is improved by the presence of catalytic amount of trifluoroacetic acid. Mechanism is discussed from the observed r

Palladium-Mediated Cyclization of 1,5-Hexadien-3-ols to 1-Methyl-1,3-cyclopentadienes

Treatment of 1-allyl-2-alkenylidenecyclohexanols in acetic acid by the Pd(0) complex led to 8-methyl bicyclonona-1(6),7-dienes.In contrast, only few examples of cyclization vs elimination were observed in acyclic 1,5-hexadien-3-ols.Keyw

Stereochemistry of Addition of Allyl Grignard Reagents to (R)-(+)-Pulegone and Other α,β-Ethylenic Ketones

The 1,2-addition of allyl, crotyl, and 2-methyl-2-butenyl Grignard reagents to (R)-(+)-pulegone is regio- and stereoselective.In contrast 3-penten-2-yl and 3-methyl-2-butenyl Grignard reagents undergo 1,2- and 1,4-additions.A "compact approach" stabilized by orbital interaction is the proposed mechanism.A further confirmation was obtained with acyclic enones.