Nucleophilic and 1,3 Additions to Triazolinediones

Alfred Hassner; David Tang; Joseph Keogh

doi:10.1021/jo00874a007

Nucleophilic and 1,3 Additions to Triazolinediones

Alfred Hassner, David Tang, Joseph Keogh

State University of New York Binghamton University

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

15 Scopus citations

Abstract

Triazolinediones 1 are shown to undergo cycloaddition to vinyl azides 5 in a 1,3 manner with loss of nitrogen to form novel bicyclic heterocycles 6. Substituent effects on the vinyl carbons suggest nucleophilic attack by the β carbon of 5 on the N=N of 1. Phosphorus ylides likewise undergo nucleophilic attack on 1 followed by proton abstraction to produce ylides 14.

Original language	English
Pages (from-to)	2102-2104
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	41
Issue number	12
DOIs	https://doi.org/10.1021/jo00874a007
State	Published - 1 Jun 1976
Externally published	Yes

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@article{b66278237ab3477ab55253a65d82f049,

title = "Nucleophilic and 1,3 Additions to Triazolinediones",

abstract = "Triazolinediones 1 are shown to undergo cycloaddition to vinyl azides 5 in a 1,3 manner with loss of nitrogen to form novel bicyclic heterocycles 6. Substituent effects on the vinyl carbons suggest nucleophilic attack by the β carbon of 5 on the N=N of 1. Phosphorus ylides likewise undergo nucleophilic attack on 1 followed by proton abstraction to produce ylides 14.",

author = "Alfred Hassner and David Tang and Joseph Keogh",

year = "1976",

month = jun,

day = "1",

doi = "10.1021/jo00874a007",

language = "אנגלית",

volume = "41",

pages = "2102--2104",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

publisher = "American Chemical Society",

number = "12",

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T1 - Nucleophilic and 1,3 Additions to Triazolinediones

AU - Hassner, Alfred

AU - Tang, David

AU - Keogh, Joseph

PY - 1976/6/1

Y1 - 1976/6/1

N2 - Triazolinediones 1 are shown to undergo cycloaddition to vinyl azides 5 in a 1,3 manner with loss of nitrogen to form novel bicyclic heterocycles 6. Substituent effects on the vinyl carbons suggest nucleophilic attack by the β carbon of 5 on the N=N of 1. Phosphorus ylides likewise undergo nucleophilic attack on 1 followed by proton abstraction to produce ylides 14.

AB - Triazolinediones 1 are shown to undergo cycloaddition to vinyl azides 5 in a 1,3 manner with loss of nitrogen to form novel bicyclic heterocycles 6. Substituent effects on the vinyl carbons suggest nucleophilic attack by the β carbon of 5 on the N=N of 1. Phosphorus ylides likewise undergo nucleophilic attack on 1 followed by proton abstraction to produce ylides 14.

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AN - SCOPUS:0007050480

SN - 0022-3263

VL - 41

SP - 2102

EP - 2104

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 12

ER -

Nucleophilic and 1,3 Additions to Triazolinediones

Abstract

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