A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

Joseph Almog; Yirmi Zehavy; Shmuel Cohen

doi:10.1016/S0040-4039(03)00622-1

A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

Joseph Almog^*
, Yirmi Zehavy
, Shmuel Cohen

^*Corresponding author for this work

Institute of Chemistry

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

7 Scopus citations

Abstract

1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3-oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.

Original language	English
Pages (from-to)	3285-3288
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	16
DOIs	https://doi.org/10.1016/S0040-4039(03)00622-1
State	Published - 14 Apr 2003

Keywords

1,2-indanedione
1,3-oxathiolanes
Deprotection
Dioxa-dithiapropellanes
Mercaptoethanol
Protection

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10.1016/S0040-4039(03)00622-1

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title = "A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes",

abstract = "1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3-oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.",

keywords = "1,2-indanedione, 1,3-oxathiolanes, Deprotection, Dioxa-dithiapropellanes, Mercaptoethanol, Protection",

author = "Joseph Almog and Yirmi Zehavy and Shmuel Cohen",

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T1 - A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

AU - Almog, Joseph

AU - Zehavy, Yirmi

AU - Cohen, Shmuel

PY - 2003/4/14

Y1 - 2003/4/14

N2 - 1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3-oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.

AB - 1,2-Indanedione reacts with two equivalents of 2-mercaptoethanol to produce, instead of the expected 1,2-bis(1,3-oxathiolane), a dioxa-dithia[4.4.3] propellane. Other 1,2-indanediones produce analogous compounds. The protecting groups are removed at room temperature with NBS in aqueous acetone, to produce the original diketone.

KW - 1,2-indanedione

KW - 1,3-oxathiolanes

KW - Deprotection

KW - Dioxa-dithiapropellanes

KW - Mercaptoethanol

KW - Protection

UR - https://www.scopus.com/pages/publications/0037436905

U2 - 10.1016/S0040-4039(03)00622-1

DO - 10.1016/S0040-4039(03)00622-1

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AN - SCOPUS:0037436905

SN - 0040-4039

VL - 44

SP - 3285

EP - 3288

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 16

ER -

A novel method for protection and deprotection of the carbonyl groups in 1,2-indanedione by conversion to dioxa-dithiapropellanes

Abstract

Keywords

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