The Journal of Organic Chemistry

Halogen effect on the ring opening of pulegone hydrohalides

BK Shull, M Koreeda

Index: Shull, Brian K.; Koreeda, Masato Journal of Organic Chemistry, 1990 , vol. 55, # 7 p. 2249 - 2251

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Citation Number: 3

Abstract

The ring-opening reaction of pulegone hydrochloride (2a) with nucleophiles such as NaOH, LiNMe2, and LAH, reported by Plesek'and Overberger, 2 serves as a convenient means for the synthesis of acyclic chiral compounds (see Scheme I). In conjunction with our continuing interest in the stereocontrolled synthesis of steroid side chains? an application of this useful ring-opening reaction of a-(2-halo-2-methylethyl) cyclohexanones was envisioned.

 Related Synthetic Route
Tert-Butyllithium Structure

594-19-4

Tert-Butyllithium

2-(2-bromopropan-2-yl)-5-methylcyclohexan-1-one Structure

86613-13-0

2-(2-bromopropa...

~0%

N/A Structure

125137-92-0

N/A

Pulegone Structure

89-82-7

Pulegone

2-(2-chloropropan-2-yl)-5-methylcyclohexan-1-one Structure

66448-75-7

2-(2-chloroprop...

~79%

(R)-Citronellol Structure

1117-61-9

(R)-Citronellol

2-(2-bromopropan-2-yl)-5-methylcyclohexan-1-one Structure

86613-13-0

2-(2-bromopropa...

~60%

(R)-Citronellol Structure

1117-61-9

(R)-Citronellol

(5R)-2-(1-Iodo-1-methylethyl)-5-methylcyclohexanone Structure

86613-12-9

(5R)-2-(1-Iodo-...

~58%

(R)-Citronellol Structure

1117-61-9

(R)-Citronellol


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