Synlett 2012; 23(15): 2291-2292
DOI: 10.1055/s-0032-1317177
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© Georg Thieme Verlag Stuttgart · New York

Phenylisocyanate

Palash Pal
Pharmacy Department, The M. S. University of Baroda, Vadodara 390001, Gujarat, India   Email: palash.pal7@gmail.com
› Author Affiliations
Further Information

Publication History

Publication Date:
03 September 2012 (online)

Dedicated to my supervisor Prof. M. R. Yadav for providing me the opportunity to work with him and AICTE, New Delhi for financial assistance.

Introduction

Isocyanates are useful intermediates for a variety of reactions including nucleophilic additions with alcohols and amines to produce carbamates and ureas, respectively. They also participate in cycloadditions to generate heterocycles and polymerizations to produce commodities such as polyurethane. The high yields and lack of by-products associated with isocyanate chemistry has led to widespread application of isocyanates in the pharmaceutical, agrochemical and polymer industries.[ 1 ]

Phenylisocyanate is a colorless liquid with strong odor and causes lachrymation. Typically phenylisocyanate is generated either from aniline by reacting with phosgene or phosgene equivalents, such as diphosgene or triphosgene or via thermal dissociation of carbamic acid derivatives. Phenylisocyanate can also be generated from non-amine precursors via the rearrangement of phenyl azide (Curtius rearrangement) and hydroxamic acids (Lossen rearrangement).[ 2 ]

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Scheme 1
 
  • References

  • 1 Oh LM, Spoors PG, Goodman RM. Tetrahedron Lett. 2004; 45: 4769
  • 2 Marinescu L, Thinggaard J, Thomsen IB, Bols M. J. Org. Chem. 2003; 68: 9453
  • 3 Parcher BW, Erion DM, Dang Q. Tetrahedron Lett. 2004; 45: 2677
  • 4 Kondo T, Nomura M, Ura Y, Wada K, Mitsudo T. Tetrahedron Lett. 2006; 47: 7107
  • 5 Coskun N, Parlar A. Synth. Commun. 2006; 36: 997
  • 6 Awadallah AD. Islamic Univ. J. 2006; 14: 129
  • 7 Zhang K, Chopade PR, Louie J. Tetrahedron Lett. 2008; 49: 4306
  • 8 Chen C.-Y, Lin H.-C, Huang YY, Chen K.-L, Huang J.-J, Yeh M.-Y. Tetrahedron 2010; 66: 1892
  • 9 Veronese AC, Durini E, Bertolasi V, Basato M, Tubaro C. Tetrahedron 2010; 66: 8313
  • 10 Khandan-Barani K, Maghsoodlou MT, Hazeri N, Habibi-Khorasani SM, Sajadikhah SS. ARKIVOC 2011; (xi): 22
  • 11 Miura T, Mikano Y, Murakami M. Org. Lett. 2011; 13: 3560