Aqueous chlorination of α-terpineol

Herbert L. Kopperman; Richard C. Hallcher; Agatha Riehl; Robert M Carlson; Ronald Caple

doi:10.1016/0040-4020(76)85148-4

Aqueous chlorination of α-terpineol

Herbert L. Kopperman, Richard C. Hallcher, Agatha Riehl, Robert M Carlson, Ronald Caple

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

27 Scopus citations

Abstract

Of the multitude of products obtained upon the aqueous chlorination of α-terpineol (1), under both acidic and basic conditions, the major ones are the diequatorial trans, 4, and diaxial trans, 5, Markovnikov adducts of hypochlorous acid to the olefinic center. With the exclusion of small amounts of dichloride formation, the remainder of the products appear to be derived from 4 and 5 by hydrolysis or elimination sequences. The product distribution exhibits an expected pH dependence that is useful in the structural assignments.

Original language	English (US)
Pages (from-to)	1621-1626
Number of pages	6
Journal	Tetrahedron
Volume	32
Issue number	14
DOIs	https://doi.org/10.1016/0040-4020(76)85148-4
State	Published - 1976

Access

10.1016/0040-4020(76)85148-4

Fingerprint Dive into the research topics of 'Aqueous chlorination of α-terpineol'. Together they form a unique fingerprint.

Cite this

@article{cdb3193761334eeca7839c62222fb781,

title = "Aqueous chlorination of α-terpineol",

abstract = "Of the multitude of products obtained upon the aqueous chlorination of α-terpineol (1), under both acidic and basic conditions, the major ones are the diequatorial trans, 4, and diaxial trans, 5, Markovnikov adducts of hypochlorous acid to the olefinic center. With the exclusion of small amounts of dichloride formation, the remainder of the products appear to be derived from 4 and 5 by hydrolysis or elimination sequences. The product distribution exhibits an expected pH dependence that is useful in the structural assignments.",

author = "Kopperman, {Herbert L.} and Hallcher, {Richard C.} and Agatha Riehl and Carlson, {Robert M} and Ronald Caple",

year = "1976",

doi = "10.1016/0040-4020(76)85148-4",

language = "English (US)",

volume = "32",

pages = "1621--1626",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Limited",

number = "14",

}

TY - JOUR

T1 - Aqueous chlorination of α-terpineol

AU - Kopperman, Herbert L.

AU - Hallcher, Richard C.

AU - Riehl, Agatha

AU - Carlson, Robert M

AU - Caple, Ronald

PY - 1976

Y1 - 1976

N2 - Of the multitude of products obtained upon the aqueous chlorination of α-terpineol (1), under both acidic and basic conditions, the major ones are the diequatorial trans, 4, and diaxial trans, 5, Markovnikov adducts of hypochlorous acid to the olefinic center. With the exclusion of small amounts of dichloride formation, the remainder of the products appear to be derived from 4 and 5 by hydrolysis or elimination sequences. The product distribution exhibits an expected pH dependence that is useful in the structural assignments.

AB - Of the multitude of products obtained upon the aqueous chlorination of α-terpineol (1), under both acidic and basic conditions, the major ones are the diequatorial trans, 4, and diaxial trans, 5, Markovnikov adducts of hypochlorous acid to the olefinic center. With the exclusion of small amounts of dichloride formation, the remainder of the products appear to be derived from 4 and 5 by hydrolysis or elimination sequences. The product distribution exhibits an expected pH dependence that is useful in the structural assignments.

UR - http://www.scopus.com/inward/record.url?scp=0000871740&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000871740&partnerID=8YFLogxK

U2 - 10.1016/0040-4020(76)85148-4

DO - 10.1016/0040-4020(76)85148-4

M3 - Article

AN - SCOPUS:0000871740

VL - 32

SP - 1621

EP - 1626

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 14

ER -