Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol
Publication type: Journal Article
Publication date: 1982-11-01
scimago Q3
wos Q2
SJR: 0.423
CiteScore: 4.0
Impact factor: 2.5
ISSN: 00086215, 1873426X
Organic Chemistry
Biochemistry
General Medicine
Analytical Chemistry
Abstract
Nucleophilic addition-reactions of the title compound, prepared from the corresponding 3-nitrohex-2-enitol, were investigated under kinetically controlled conditions; such sterically bulky nucleophiles as tert -butyl peroxide and 2,4-pentanedionate ions (except in 1,4-dioxane) were found to engage almost exclusively in equatorial attack, whereas, for hydroperoxide and deuteride ions, axial atack is favored. All the products thus obtained, other than the nitro epoxides, were subjected to an equilibration test. Factors potentially controlling the addition reactions under thermodynamically, as well as kinetically, controlled conditions are discussed, based on the results described herein.
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Sakakibara T. et al. Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol // Carbohydrate Research. 1982. Vol. 109. pp. 167-179.
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Sakakibara T., Minami T., ISHIDO Y., Sudoh R. Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol // Carbohydrate Research. 1982. Vol. 109. pp. 167-179.
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TY - JOUR
DO - 10.1016/0008-6215(82)84037-8
UR - https://doi.org/10.1016/0008-6215(82)84037-8
TI - Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol
T2 - Carbohydrate Research
AU - Sakakibara, Tohru
AU - Minami, Toshiaki
AU - ISHIDO, Yoshiharu
AU - Sudoh, Rokuro
PY - 1982
DA - 1982/11/01
PB - Elsevier
SP - 167-179
VL - 109
SN - 0008-6215
SN - 1873-426X
ER -
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@article{1982_Sakakibara,
author = {Tohru Sakakibara and Toshiaki Minami and Yoshiharu ISHIDO and Rokuro Sudoh},
title = {Preparation, and nucleophilic addition-reactions, of 1,5- anhydro-4,6-O-benzylidene-2,3-dideoxy-2-nitro-d-erythro-hex-2-enitol},
journal = {Carbohydrate Research},
year = {1982},
volume = {109},
publisher = {Elsevier},
month = {nov},
url = {https://doi.org/10.1016/0008-6215(82)84037-8},
pages = {167--179},
doi = {10.1016/0008-6215(82)84037-8}
}