THE UNUSUAL REACTION OF TETRACHLOROTHIOPHENE DIOXIDE WITH AN ADDUCT OF 5,6-BISMETHYLENENORBORNENE AND HEXACHLORONORBORNADIENE

E C  GRAVETT; J A K  HOWARD; K  MACKENZIE; S X  LIU; P B  KARADAKOV

THE UNUSUAL REACTION OF TETRACHLOROTHIOPHENE DIOXIDE WITH AN ADDUCT OF 5,6-BISMETHYLENENORBORNENE AND HEXACHLORONORBORNADIENE

E C GRAVETT, J A K HOWARD, K MACKENZIE, S X LIU, P B KARADAKOV

Chemistry

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

Abstract

Hexachloronorbornadiene forms a 1:1 adduct 3 with 5,6-bismethylenenorbornene, which, on reaction with 1,2,3,4-tetrachlorothiophene dioxide, yields by loss of SO2, cycloreversion and further cycloaddition two compounds shown by mass, C-13 NMR and H-1 NMR spectroscopy and a single-crystal X-ray structure determination to be the isomeric products of a rare type of specific diene-capture by perchlorothiophene dioxide; a rational explanation for this and other examples is proposed, and a further example of norbornene sp2 C pyramidalisation is disclosed.

Original language	English
Pages (from-to)	1763-1767
Number of pages	5
Journal	JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS
Issue number	24
Publication status	Published - 15 Dec 1991

Keywords

DIELS-ALDER REACTION
DOUBLE-BOND
THIOPHENE
DERIVATIVES
1,1-DIOXIDE
PARALLEL

Cite this

@article{e024d330207c421881bc261605cf3dea,

title = "THE UNUSUAL REACTION OF TETRACHLOROTHIOPHENE DIOXIDE WITH AN ADDUCT OF 5,6-BISMETHYLENENORBORNENE AND HEXACHLORONORBORNADIENE",

abstract = "Hexachloronorbornadiene forms a 1:1 adduct 3 with 5,6-bismethylenenorbornene, which, on reaction with 1,2,3,4-tetrachlorothiophene dioxide, yields by loss of SO2, cycloreversion and further cycloaddition two compounds shown by mass, C-13 NMR and H-1 NMR spectroscopy and a single-crystal X-ray structure determination to be the isomeric products of a rare type of specific diene-capture by perchlorothiophene dioxide; a rational explanation for this and other examples is proposed, and a further example of norbornene sp2 C pyramidalisation is disclosed.",

keywords = "DIELS-ALDER REACTION, DOUBLE-BOND, THIOPHENE, DERIVATIVES, 1,1-DIOXIDE, PARALLEL",

author = "GRAVETT, {E C} and HOWARD, {J A K} and K MACKENZIE and LIU, {S X} and KARADAKOV, {P B}",

year = "1991",

month = dec,

day = "15",

language = "English",

pages = "1763--1767",

journal = "JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS",

issn = "0022-4936",

publisher = "Chemical Society",

number = "24",

}

TY - JOUR

T1 - THE UNUSUAL REACTION OF TETRACHLOROTHIOPHENE DIOXIDE WITH AN ADDUCT OF 5,6-BISMETHYLENENORBORNENE AND HEXACHLORONORBORNADIENE

AU - GRAVETT, E C

AU - HOWARD, J A K

AU - MACKENZIE, K

AU - LIU, S X

AU - KARADAKOV, P B

PY - 1991/12/15

Y1 - 1991/12/15

N2 - Hexachloronorbornadiene forms a 1:1 adduct 3 with 5,6-bismethylenenorbornene, which, on reaction with 1,2,3,4-tetrachlorothiophene dioxide, yields by loss of SO2, cycloreversion and further cycloaddition two compounds shown by mass, C-13 NMR and H-1 NMR spectroscopy and a single-crystal X-ray structure determination to be the isomeric products of a rare type of specific diene-capture by perchlorothiophene dioxide; a rational explanation for this and other examples is proposed, and a further example of norbornene sp2 C pyramidalisation is disclosed.

AB - Hexachloronorbornadiene forms a 1:1 adduct 3 with 5,6-bismethylenenorbornene, which, on reaction with 1,2,3,4-tetrachlorothiophene dioxide, yields by loss of SO2, cycloreversion and further cycloaddition two compounds shown by mass, C-13 NMR and H-1 NMR spectroscopy and a single-crystal X-ray structure determination to be the isomeric products of a rare type of specific diene-capture by perchlorothiophene dioxide; a rational explanation for this and other examples is proposed, and a further example of norbornene sp2 C pyramidalisation is disclosed.

KW - DIELS-ALDER REACTION

KW - DOUBLE-BOND

KW - THIOPHENE

KW - DERIVATIVES

KW - 1,1-DIOXIDE

KW - PARALLEL

M3 - Article

SN - 0022-4936

SP - 1763

EP - 1767

JO - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

JF - JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS

IS - 24

ER -