Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels-Alder/Ramberg-Bäcklund Reactions

Eric Block; Hak Rim Jeon; Shao Zhong Zhang; Evgeny V. Dikarev

doi:10.1021/ol0363523

Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels-Alder/Ramberg-Bäcklund Reactions

Eric Block
, Hak Rim Jeon
, Shao Zhong Zhang
, Evgeny V. Dikarev

Chemistry

University at Albany

SUNY Albany

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

8 Scopus citations

Abstract

(Matrix presented) Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH₂-SCl or Cl₂CHSCl, respectively, followed by NaHCO₃ dehydrochlorination. With dienes, 3a gave Diels-Alder adducts that, with base, underwent Ramberg-Bäcklund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels-Alder adducts that, with base in the presence of the novel chlorine source MeSO₂CCl₃, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2- diene.

Original language	English
Pages (from-to)	437-440
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	3
DOIs	https://doi.org/10.1021/ol0363523
State	Published - Feb 5 2004

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title = "Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels-Alder/Ramberg-B{\"a}cklund Reactions",

abstract = "(Matrix presented) Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH2-SCl or Cl2CHSCl, respectively, followed by NaHCO3 dehydrochlorination. With dienes, 3a gave Diels-Alder adducts that, with base, underwent Ramberg-B{\"a}cklund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels-Alder adducts that, with base in the presence of the novel chlorine source MeSO2CCl3, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2- diene.",

author = "Eric Block and Jeon, \{Hak Rim\} and Zhang, \{Shao Zhong\} and Dikarev, \{Evgeny V.\}",

year = "2004",

month = feb,

day = "5",

doi = "10.1021/ol0363523",

language = "English",

volume = "6",

pages = "437--440",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "3",

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TY - JOUR

T1 - Chloromethanesulfonylethene and Dichloromethanesulfonylethene

T2 - New Reagents for Tandem Diels-Alder/Ramberg-Bäcklund Reactions

AU - Block, Eric

AU - Jeon, Hak Rim

AU - Zhang, Shao Zhong

AU - Dikarev, Evgeny V.

PY - 2004/2/5

Y1 - 2004/2/5

N2 - (Matrix presented) Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH2-SCl or Cl2CHSCl, respectively, followed by NaHCO3 dehydrochlorination. With dienes, 3a gave Diels-Alder adducts that, with base, underwent Ramberg-Bäcklund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels-Alder adducts that, with base in the presence of the novel chlorine source MeSO2CCl3, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2- diene.

AB - (Matrix presented) Chloromethanesulfonylethene (3a) and dichloromethanesulfonylethene (3b) were prepared by oxidation of the adducts of ethylene and ClCH2-SCl or Cl2CHSCl, respectively, followed by NaHCO3 dehydrochlorination. With dienes, 3a gave Diels-Alder adducts that, with base, underwent Ramberg-Bäcklund reaction, giving products corresponding to the adducts of the dienes and allene. Similarly, 3b gave Diels-Alder adducts that, with base in the presence of the novel chlorine source MeSO2CCl3, cleanly afforded products corresponding to the adducts of the dienes and 1,1-dichloropropa-1,2- diene.

UR - https://www.scopus.com/pages/publications/1342264119

U2 - 10.1021/ol0363523

DO - 10.1021/ol0363523

M3 - Article

SN - 1523-7060

VL - 6

SP - 437

EP - 440

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Chloromethanesulfonylethene and Dichloromethanesulfonylethene: New Reagents for Tandem Diels-Alder/Ramberg-Bäcklund Reactions

Abstract

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