Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates

Felicity I. McLure; Robert K. Norris; Karen Wilson

doi:10.1071/CH9870049

Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates

Felicity I. McLure, Robert K. Norris, Karen Wilson

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

Abstract

The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic, were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an S_N1-like, an S_N(AEAE) and an S_RN1 process respectively.

Original language	English
Pages (from-to)	49-60
Number of pages	12
Journal	Australian Journal of Chemistry
Volume	40
Issue number	1
DOIs	https://doi.org/10.1071/CH9870049
Publication status	Published - 1987
Externally published	Yes

Access to Document

10.1071/CH9870049

Cite this

@article{cb473409390c40a388c0f69d293295e4,

title = "Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates",

abstract = "The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic, were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRN1 process respectively.",

author = "McLure, {Felicity I.} and Norris, {Robert K.} and Karen Wilson",

year = "1987",

doi = "10.1071/CH9870049",

language = "English",

volume = "40",

pages = "49--60",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

publisher = "CSIRO Publishing",

number = "1",

}

TY - JOUR

T1 - Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates

AU - McLure, Felicity I.

AU - Norris, Robert K.

AU - Wilson, Karen

PY - 1987

Y1 - 1987

N2 - The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic, were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRN1 process respectively.

AB - The reaction of the chlorides (4)-(6), which are both neopentylic and thenylic, were studied. The chloride (4), unlike its analogue (13) in the benzene series, undergoes ready solvolysis with alcohols to give the corresponding ethers, e.g. (7)-(9). The chlorides (5) and (6) react more slowly than (4) but undergo methanolysis to give the methyl ethers (11) and (12) respectively. In the dipolar aprotic solvents, dimethyl sulfoxide and dimethylformamide, the reactions of the chlorides (4), (5) and (6) with the thiolate salt (16) appear to proceed by an SN1-like, an SN(AEAE) and an SRN1 process respectively.

UR - http://www.scopus.com/inward/record.url?scp=84970588576&partnerID=8YFLogxK

U2 - 10.1071/CH9870049

DO - 10.1071/CH9870049

M3 - Article

AN - SCOPUS:84970588576

VL - 40

SP - 49

EP - 60

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

SN - 0004-9425

IS - 1

ER -

Nucleophilic Substitution Reactions of Thienyl Neopentyl Substrates

Abstract

Access to Document

Other files and links

Fingerprint

Cite this