Cleavage of benzyl ethers by triphenylphosphine hydrobromide

Mani Ramanathan; Duen Ren Hou

doi:10.1016/j.tetlet.2010.09.065

Cleavage of benzyl ethers by triphenylphosphine hydrobromide

Mani Ramanathan, Duen Ren Hou

Department of Chemistry

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

13 Scopus citations

Abstract

Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3° alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh₃·HBr offers a new and effective method for the deprotection of benzyl ethers.

Original language	English
Pages (from-to)	6143-6145
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2010.09.065
State	Published - 24 Nov 2010

Access to Document

10.1016/j.tetlet.2010.09.065

Cite this

@article{d9a0f65a3c674dadb20bc3a62ffd091c,

title = "Cleavage of benzyl ethers by triphenylphosphine hydrobromide",

abstract = "Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3° alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh3·HBr offers a new and effective method for the deprotection of benzyl ethers.",

author = "Mani Ramanathan and Hou, {Duen Ren}",

note = "Funding Information: This research was supported by the National Science Council (NSC 98-2113-M-008-001-MY3 ), Taiwan, ROC. The authors are grateful to Ms. Ping-Yu Lin at the Institute of Chemistry, Academia Sinica and Valuable Instrument Center in National Central University for obtaining mass analysis. ",

year = "2010",

month = nov,

day = "24",

doi = "10.1016/j.tetlet.2010.09.065",

language = "???core.languages.en_GB???",

volume = "51",

pages = "6143--6145",

journal = "Tetrahedron Letters",

issn = "0040-4039",

number = "47",

}

TY - JOUR

T1 - Cleavage of benzyl ethers by triphenylphosphine hydrobromide

AU - Ramanathan, Mani

AU - Hou, Duen Ren

N1 - Funding Information: This research was supported by the National Science Council (NSC 98-2113-M-008-001-MY3 ), Taiwan, ROC. The authors are grateful to Ms. Ping-Yu Lin at the Institute of Chemistry, Academia Sinica and Valuable Instrument Center in National Central University for obtaining mass analysis.

PY - 2010/11/24

Y1 - 2010/11/24

N2 - Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3° alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh3·HBr offers a new and effective method for the deprotection of benzyl ethers.

AB - Triphenylphosphine hydrobromide was found to cleave the benzyl ethers derived from 1°, 2° alkyl, and aryl alcohols to the corresponding alcohols and benzyltriphenylphosphonium bromide in good yields. Alkene and allyl phosphonium salts were produced from the benzyl ethers with 3° alkyl and allyl groups, respectively. These results indicate that the formation of the product is determined by the relative stability of the carbocationic intermediate. The anhydrous, stoichiometric amount of PPh3·HBr offers a new and effective method for the deprotection of benzyl ethers.

UR - http://www.scopus.com/inward/record.url?scp=77958461204&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.09.065

DO - 10.1016/j.tetlet.2010.09.065

M3 - 期刊論文

AN - SCOPUS:77958461204

SN - 0040-4039

VL - 51

SP - 6143

EP - 6145

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 47

ER -

Cleavage of benzyl ethers by triphenylphosphine hydrobromide

Abstract

Access to Document

Fingerprint

Cite this