gem-difluorination vs 1,3-dithiolane-dihydro-1,4-dithiin rearrangement. The role of benzylic carbons

J. Jekó́, Tibor Timár, Joseph Cs Jaszberenyi

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

1,3-Dithiolanes bearing a phenyl or substituted aromatic group and a methyl (or methylene) group attached to C-2 cannot be gem-difluorinated with 1,3-dibromo-5,5-dimethylhydantoin (DBH) (or NBS) + HF/pyridine because a rapid 1,3-dithiolane-dihydro-1,4-dithiin rearrangement takes place instead.

Original languageEnglish
Pages (from-to)6748-6751
Number of pages4
JournalJournal of Organic Chemistry
Volume56
Issue number24
Publication statusPublished - 1991

Fingerprint

Gems
Bearings (structural)
Carbon
1,3-dithiolane
1,3-dibromo-5,5-dimethylhydantoin
pyridine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

gem-difluorination vs 1,3-dithiolane-dihydro-1,4-dithiin rearrangement. The role of benzylic carbons. / Jekó́, J.; Timár, Tibor; Jaszberenyi, Joseph Cs.

In: Journal of Organic Chemistry, Vol. 56, No. 24, 1991, p. 6748-6751.

Research output: Contribution to journalArticle

@article{45986676c67e4c9c98567e3b1b349138,
title = "gem-difluorination vs 1,3-dithiolane-dihydro-1,4-dithiin rearrangement. The role of benzylic carbons",
abstract = "1,3-Dithiolanes bearing a phenyl or substituted aromatic group and a methyl (or methylene) group attached to C-2 cannot be gem-difluorinated with 1,3-dibromo-5,5-dimethylhydantoin (DBH) (or NBS) + HF/pyridine because a rapid 1,3-dithiolane-dihydro-1,4-dithiin rearrangement takes place instead.",
author = "J. Jek{\'o}́ and Tibor Tim{\'a}r and Jaszberenyi, {Joseph Cs}",
year = "1991",
language = "English",
volume = "56",
pages = "6748--6751",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "24",

}

TY - JOUR

T1 - gem-difluorination vs 1,3-dithiolane-dihydro-1,4-dithiin rearrangement. The role of benzylic carbons

AU - Jekó́, J.

AU - Timár, Tibor

AU - Jaszberenyi, Joseph Cs

PY - 1991

Y1 - 1991

N2 - 1,3-Dithiolanes bearing a phenyl or substituted aromatic group and a methyl (or methylene) group attached to C-2 cannot be gem-difluorinated with 1,3-dibromo-5,5-dimethylhydantoin (DBH) (or NBS) + HF/pyridine because a rapid 1,3-dithiolane-dihydro-1,4-dithiin rearrangement takes place instead.

AB - 1,3-Dithiolanes bearing a phenyl or substituted aromatic group and a methyl (or methylene) group attached to C-2 cannot be gem-difluorinated with 1,3-dibromo-5,5-dimethylhydantoin (DBH) (or NBS) + HF/pyridine because a rapid 1,3-dithiolane-dihydro-1,4-dithiin rearrangement takes place instead.

UR - http://www.scopus.com/inward/record.url?scp=0343727155&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0343727155&partnerID=8YFLogxK

M3 - Article

AN - SCOPUS:0343727155

VL - 56

SP - 6748

EP - 6751

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 24

ER -