Silylcarbocyclizations of 1,6-diynes

Iwao Ojima; Jiawang Zhu; Ephraim S. Vidal; Dora Fracchiolla Kass

doi:10.1021/ja980907l

Silylcarbocyclizations of 1,6-diynes

Iwao Ojima
, Jiawang Zhu
, Ephraim S. Vidal
, Dora Fracchiolla Kass

Chemistry

Stony Brook University

Stony Brook University

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

77 Scopus citations

Abstract

Two types of silylcarbocyclization reactions (SiCaCs) of 1,6-diynes are discussed: (i) silylcarbocyclization-hydrosilylation (SiCaC-HS) reactions giving 3-(silylmethylene)-4-(silylmethyl)pyrrolidine, 3-(silylmethylene)-4-(silylmethyl)tetrahydrofuran, 3,4-bis(silylmethyl)-3-pyrroline, and 1,2-bis(silylmethyl)-4,4-dicarbethoxycyclopentene; and (ii) silylcarbobicyclization (SiCaB) reactions yielding a variety of carbocyclic and heterocyclic bicyclo[3.3.0] systems. Mechanisms for these SiCaC-HS and SiCaB processes are proposed.

Original language	English
Pages (from-to)	6690-6697
Number of pages	8
Journal	Journal of the American Chemical Society
Volume	120
Issue number	27
DOIs	https://doi.org/10.1021/ja980907l
State	Published - Jul 15 1998

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title = "Silylcarbocyclizations of 1,6-diynes",

abstract = "Two types of silylcarbocyclization reactions (SiCaCs) of 1,6-diynes are discussed: (i) silylcarbocyclization-hydrosilylation (SiCaC-HS) reactions giving 3-(silylmethylene)-4-(silylmethyl)pyrrolidine, 3-(silylmethylene)-4-(silylmethyl)tetrahydrofuran, 3,4-bis(silylmethyl)-3-pyrroline, and 1,2-bis(silylmethyl)-4,4-dicarbethoxycyclopentene; and (ii) silylcarbobicyclization (SiCaB) reactions yielding a variety of carbocyclic and heterocyclic bicyclo[3.3.0] systems. Mechanisms for these SiCaC-HS and SiCaB processes are proposed.",

author = "Iwao Ojima and Jiawang Zhu and Vidal, \{Ephraim S.\} and Kass, \{Dora Fracchiolla\}",

year = "1998",

month = jul,

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doi = "10.1021/ja980907l",

language = "English",

volume = "120",

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journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Silylcarbocyclizations of 1,6-diynes

AU - Ojima, Iwao

AU - Zhu, Jiawang

AU - Vidal, Ephraim S.

AU - Kass, Dora Fracchiolla

PY - 1998/7/15

Y1 - 1998/7/15

N2 - Two types of silylcarbocyclization reactions (SiCaCs) of 1,6-diynes are discussed: (i) silylcarbocyclization-hydrosilylation (SiCaC-HS) reactions giving 3-(silylmethylene)-4-(silylmethyl)pyrrolidine, 3-(silylmethylene)-4-(silylmethyl)tetrahydrofuran, 3,4-bis(silylmethyl)-3-pyrroline, and 1,2-bis(silylmethyl)-4,4-dicarbethoxycyclopentene; and (ii) silylcarbobicyclization (SiCaB) reactions yielding a variety of carbocyclic and heterocyclic bicyclo[3.3.0] systems. Mechanisms for these SiCaC-HS and SiCaB processes are proposed.

AB - Two types of silylcarbocyclization reactions (SiCaCs) of 1,6-diynes are discussed: (i) silylcarbocyclization-hydrosilylation (SiCaC-HS) reactions giving 3-(silylmethylene)-4-(silylmethyl)pyrrolidine, 3-(silylmethylene)-4-(silylmethyl)tetrahydrofuran, 3,4-bis(silylmethyl)-3-pyrroline, and 1,2-bis(silylmethyl)-4,4-dicarbethoxycyclopentene; and (ii) silylcarbobicyclization (SiCaB) reactions yielding a variety of carbocyclic and heterocyclic bicyclo[3.3.0] systems. Mechanisms for these SiCaC-HS and SiCaB processes are proposed.

UR - https://www.scopus.com/pages/publications/0032528237

U2 - 10.1021/ja980907l

DO - 10.1021/ja980907l

M3 - Article

SN - 0002-7863

VL - 120

SP - 6690

EP - 6697

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27

ER -

Silylcarbocyclizations of 1,6-diynes

Abstract

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