Synthesis and Structure of Systems Containing Pyramidalized and Strained Double Bond: An Investigation on the Cycloaddition Reactions of cisand trans-3,8-dicarbomethoxy-3,8-dihydroheptalene

Synthesis and Structure of Systems Conta And

Makale detayları

Synthesis and Structure of Systems Containing Pyramidalized and Strained Double Bond: An Investigation on the Cycloaddition Reactions of cisand trans-3,8-dicarbomethoxy-3,8-dihydroheptalene

Yazarlar:

Synthesis and Structure of Systems Conta And

Yayıncı:

TUBITAK

Ana Başlıklar:

Kimya ve ilgili bilimler

Dergi:

Turkish Journal of Chemistry 2001 Vol.25 Issue 1, pp.123-133

Belge Tipi:

Makale

Yayın Tarihi:

12/2000

Belge Dili:

İngilizce

Document ID (Org No.):

2000730203

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527

Özet:

 

The cycloaddition reactions of   cis-3,8-dicarbomethoxy-3,8-dihydroheptalene    cis-2 and  trans-3,8-dicarbomethoxy-3,8-dihydroheptalene    trans-2 with various dienophiles such as  dimethyl acetylenedicarboxylate (DMAD), p-benzoquinone, maleic  anhydride, tetracyanoethylene, naphtoquinone gave monoaddition  products  15-23.  Further addition of benzyne and dimethyl  acetylenedicarboxylate to  18 resulted in the formation of  the compounds   syn-25 and    syn-26 having pyramidalized double bonds.  The addition of benzyne  to 21 and the addition of dimethyl acetylenedicarboxylate to   21, 22 and  23 gave the anti configuration  products   anti-26,  27 and   28, respectively.  X-ray structures of   syn-25,    syn-26 and   anti-26 show  the pyramidalized angles to be 16.5o, 19.9o and  8.0o, respectively.

 

The cycloaddition reactions of   cis-3,8-dicarbomethoxy-3,8-dihydroheptalene    cis-2 and  trans-3,8-dicarbomethoxy-3,8-dihydroheptalene    trans-2 with various dienophiles such as  dimethyl acetylenedicarboxylate (DMAD), p-benzoquinone, maleic  anhydride, tetracyanoethylene, naphtoquinone gave monoaddition  products  15-23.  Further addition of benzyne and dimethyl  acetylenedicarboxylate to  18 resulted in the formation of  the compounds   syn-25 and    syn-26 having pyramidalized double bonds.  The addition of benzyne  to 21 and the addition of dimethyl acetylenedicarboxylate to   21, 22 and  23 gave the anti configuration  products   anti-26,  27 and   28, respectively.  X-ray structures of   syn-25,    syn-26 and   anti-26 show  the pyramidalized angles to be 16.5o, 19.9o and  8.0o, respectively.

Makale detayları

Synthesis and Structure of Systems Containing Pyramidalized and Strained Double Bond: An Investigation on the Cycloaddition Reactions of cisand trans-3,8-dicarbomethoxy-3,8-dihydroheptalene

Yazarlar: Synthesis and Structure of Systems Conta And

Yayıncı: TUBITAK

Ana Başlıklar: Kimya ve ilgili bilimler

Dergi: Turkish Journal of Chemistry 2001 Vol.25 Issue 1, pp.123-133

Belge Tipi: Makale

Yayın Tarihi: 12/2000

Belge Dili: İngilizce

Document ID (Org No.): 2000730203

Sıklık: İki Aylık

eISSN: 1303-6130

pISSN: 1300-0527

Sayı

Yazarlar:

Synthesis and Structure of Systems Conta And

Yayıncı:

TUBITAK

Ana Başlıklar:

Kimya ve ilgili bilimler

Dergi:

Turkish Journal of Chemistry 2001 Vol.25 Issue 1, pp.123-133

Belge Tipi:

Makale

Yayın Tarihi:

12/2000

Belge Dili:

İngilizce

Document ID (Org No.):

2000730203

Sıklık:

İki Aylık

eISSN:

1303-6130

pISSN:

1300-0527